S1
SUPPORTING INFORMATION
Chiral bicyclic skeleton-tethered bipyridine–Zn(OTf)2 complex as Lewis acid: Enantioselective Friedel–Crafts alkylation of indoles with nitroalkenes
Kesa Venkatanna, Santhakumar Yeswanth Kumar, Muthupandi Karthick, Ramanathan
Padmanaban, Chinnasamy Ramaraj Ramanathan*
Department of Chemistry, Pondicherry University, Puducherry – 605 014, India.
E-mail: [email protected]
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019
S2
Data:
S. No. Details Page No.
1. Copies of 1H NMR spectra of compounds, 2a-2q S4 – S12
2. Copies of 1H, 13C NMR spectra of compounds, 3a-3s S14 – S32
3. HPLC chromatogram of compounds, 3a-3s S34 – S72
4. Comparison of observed and reported optical rotations for 3a-3s S73 – S74
5. Cartesian Coordinates for CRCB tethered bipyridine-Zn--nitrostyrene
complex I
S75 – S77
S3
1. Copies of 1H NMR spectra of
compounds, 2a-2q
S4
11 10 9 8 7 6 5 4 3 2 1 0 ppm
7.260
7.436
7.453
7.457
7.468
7.471
7.484
7.487
7.491
7.505
7.540
7.544
7.549
7.561
7.571
7.605
7.992
8.027
2.00
0.90
1.99
1.12
1.00
Current Data ParametersNAME KV-IV-685EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160708Time 15.52INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 298.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
11 10 9 8 7 6 5 4 3 2 1 ppm
1.576
3.955
6.969
6.991
7.003
7.006
7.022
7.024
7.041
7.043
7.260
7.443
7.447
7.462
7.466
7.479
7.484
7.867
7.901
8.127
8.161
3.01
1.04
1.08
2.13
1.00
1.02
Current Data ParametersNAME KV-V-763EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170105Time 16.55INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S5
10 9 8 7 6 5 4 3 2 1 0 ppm
3.848
7.032
7.047
7.129
7.148
7.260
7.343
7.364
7.384
7.549
7.583
7.948
7.982
2.94
2.05
1.06
1.05
1.02
1.00
Current Data ParametersNAME MK-3-OME-NSEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190122Time 14.20INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 295.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300045 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
11 10 9 8 7 6 5 4 3 2 1 ppm
1.594
3.866
6.942
6.965
7.260
7.490
7.498
7.512
7.532
7.954
7.988
3.00
1.97
3.01
0.98
Current Data ParametersNAME KV-IV-684EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160708Time 15.26INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 298.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S6
1234567891011 ppm
1.575
7.260
7.320
7.324
7.339
7.343
7.358
7.363
7.365
7.370
7.385
7.388
7.404
7.407
7.521
7.555
7.564
7.569
7.583
7.587
7.673
7.681
7.684
7.700
7.704
8.384
8.418
2.26
1.08
1.04
0.95
1.00
Current Data ParametersNAME KV-V-792EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170213Time 13.45INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 293.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
9 8 7 6 5 4 3 2 1 ppm
7.260
7.317
7.337
7.356
7.468
7.487
7.541
7.576
7.611
7.616
7.618
7.631
7.636
7.693
7.697
7.702
7.911
1.06
1.03
1.04
0.95
1.02
1.00
Current Data ParametersNAME KV-VI-991EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20171109Time 16.25INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 295.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S7
11 10 9 8 7 6 5 4 3 2 1 ppm
1.572
7.260
7.406
7.427
7.559
7.590
7.593
7.611
7.931
7.965
2.05
1.96
0.80
1.00
Current Data ParametersNAME KV-V-806EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170303Time 16.32INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 322DW 60.800 usecDE 6.00 usecTE 292.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.409
7.246
7.260
7.266
7.434
7.454
7.549
7.583
7.967
8.001
3.00
2.03
1.96
0.95
0.94
Current Data ParametersNAME KV-VI-916EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170819Time 21.33INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 203DW 60.800 usecDE 6.00 usecTE 294.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S8
9 8 7 6 5 4 3 2 1 0 ppm
1.635
7.260
7.392
7.411
7.422
7.441
7.449
7.454
7.472
7.524
7.542
7.577
7.909
7.943
3.31
1.02
1.11
1.00
Current Data ParametersNAME MK-3L-NSEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190122Time 14.32INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 295.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300046 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
11 10 9 8 7 6 5 4 3 2 1 ppm
1.583
7.260
7.424
7.440
7.446
7.450
7.481
7.487
7.503
7.545
7.579
7.947
7.981
1.97
2.06
1.05
1.00
Current Data ParametersNAME KV-V-780EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170209Time 15.08INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 293.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S9
11 10 9 8 7 6 5 4 3 2 1 ppm
7.123
7.131
7.136
7.148
7.152
7.156
7.160
7.168
7.173
7.181
7.260
7.517
7.537
7.544
7.551
7.557
7.562
7.566
7.574
7.579
7.587
7.964
7.998
2.09
3.18
1.00
Current Data ParametersNAME KV-VI-982EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20171030Time 15.27INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 295.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
9 8 7 6 5 4 3 2 1 ppm
7.260
7.656
7.666
7.686
7.690
7.706
7.865
7.884
8.038
8.072
8.339
8.342
8.345
8.347
8.360
8.362
8.365
8.368
2.27
1.03
1.05
1.11
1.00
Current Data ParametersNAME KV-VI-973-aEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20171019Time 15.53INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 256DW 60.800 usecDE 6.00 usecTE 293.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S10
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.409
7.246
7.260
7.266
7.434
7.454
7.549
7.583
7.967
8.001
3.00
2.03
1.96
0.95
0.94
Current Data ParametersNAME KV-VI-916EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170819Time 21.33INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 203DW 60.800 usecDE 6.00 usecTE 294.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
123456789 ppm
1.601
7.260
7.506
7.525
7.545
7.574
7.577
7.592
7.594
7.598
7.602
7.612
7.615
7.622
7.632
7.635
7.642
7.649
7.653
7.656
7.660
7.670
7.676
7.700
7.752
7.769
7.913
7.916
7.933
7.935
7.936
7.990
7.993
7.999
8.007
8.011
8.020
8.128
8.129
8.149
8.828
8.861
1.06
1.06
2.21
0.99
1.37
1.12
1.06
1.00
Current Data ParametersNAME KV-V-800EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170217Time 10.56INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 292.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S11
11 10 9 8 7 6 5 4 3 2 1 ppm
1.588
7.260
7.546
7.550
7.564
7.567
7.579
7.582
7.584
7.587
7.598
7.603
7.608
7.616
7.619
7.685
7.719
7.859
7.878
7.888
7.893
7.899
7.910
8.021
8.149
8.183
3.07
0.97
3.09
1.00
0.95
Current Data ParametersNAME KV-V-782EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170206Time 15.34INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
11 10 9 8 7 6 5 4 3 2 1 ppm
1.591
6.569
6.573
6.578
6.582
6.887
6.896
7.260
7.506
7.539
7.589
7.593
7.758
7.791
1.02
0.99
0.98
0.97
1.00
Current Data ParametersNAME KV-V-769EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170210Time 16.37INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S12
11 10 9 8 7 6 5 4 3 2 1 ppm
1.590
7.138
7.147
7.150
7.160
7.260
7.451
7.463
7.497
7.558
7.571
8.137
8.170
1.00
2.00
1.03
1.00
Current Data ParametersNAME KV-V-777EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170131Time 11.24INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
S13
2. Copies of 1H, 13C NMR spectra of
compounds, 3a-3s
S14
11 10 9 8 7 6 5 4 3 2 1 ppm
0.000
4.838
4.859
4.870
4.891
4.964
4.983
4.995
5.014
5.094
5.114
5.134
6.943
6.947
6.979
6.981
6.999
7.016
7.019
7.099
7.102
7.120
7.122
7.137
7.140
7.174
7.179
7.185
7.192
7.198
7.220
7.234
7.240
7.250
7.256
7.265
7.285
7.358
7.378
1.01
1.03
1.00
1.00
1.03
1.01
1.19
5.12
1.02
0.81
Current Data ParametersNAME KV-V-727EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161024Time 10.50INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 292.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300394 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
41.67
76.84
77.16
77.48
79.65
111.51
114.55
119.06
120.09
121.73
122.83
126.22
127.70
127.90
129.06
136.61
139.30 Current Data Parameters
NAME KV-V-727EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161024Time 13.03INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 28.5DW 20.800 usecDE 6.00 usecTE 293.1 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127566 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S15
11 10 9 8 7 6 5 4 3 2 1 ppm
3.831
4.867
4.889
4.898
4.921
4.935
4.952
4.967
4.984
5.507
5.524
5.528
5.546
6.736
6.755
6.773
6.831
6.852
6.970
6.988
7.007
7.015
7.023
7.083
7.101
7.121
7.130
7.133
7.151
7.170
7.240
7.260
7.383
7.403
8.017
3.01
2.00
0.97
0.99
1.01
2.89
1.05
1.19
1.07
1.01
0.83
Current Data ParametersNAME KV-V-788-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170314Time 16.05INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536
SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 293.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300409 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
35.62
55.65
76.84
77.16
77.48
78.23
110.91
111.39
114.00
119.21
119.84
120.90
122.09
122.57
126.63
127.30
128.77
129.06
136.51
156.98 Current Data Parameters
NAME KV-V-788-AEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170314Time 16.35INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 50.8DW 20.800 usecDE 6.00 usecTE 293.8 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127589 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S16
10 9 8 7 6 5 4 3 2 1 ppm
3.763
4.907
4.928
4.939
4.960
5.027
5.046
5.059
5.078
5.147
5.167
5.187
6.783
6.784
6.789
6.804
6.810
6.873
6.929
6.949
7.028
7.034
7.066
7.086
7.104
7.180
7.182
7.200
7.218
7.220
7.228
7.247
7.260
7.267
7.343
7.364
7.464
7.484
8.139
3.00
1.03
1.04
0.99
1.01
1.03
1.02
1.02
0.99
1.34
1.04
0.97
1.01
0.85
Current Data ParametersNAME KV-V-825EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170317Time 8.57INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 290.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
200 180 160 140 120 100 80 60 40 20 ppm
41.62
55.33
76.84
77.16
77.48
79.56
111.51
112.61
114.13
114.38
119.01
120.07
120.14
121.72
122.81
126.21
130.06
136.57
140.92
160.02 Current Data Parameters
NAME KV-V-825
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170319
Time 11.00
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 512
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631988 sec
RG 50.8
DW 20.800 usec
DE 6.00 usec
TE 290.5 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.15 usec
PL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.90 dB
PL13 14.90 dB
PL2 -3.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127577 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S17
2345678910 ppm3.775
4.873
4.894
4.904
4.925
5.026
5.044
5.056
5.075
5.121
5.141
6.838
6.844
6.855
6.860
6.868
7.023
7.029
7.056
7.058
7.076
7.094
7.096
7.178
7.181
7.199
7.216
7.219
7.237
7.242
7.255
7.260
7.351
7.372
7.425
7.445
8.103
3.06
1.00
1.00
1.01
1.88
0.96
1.03
1.07
2.25
0.96
0.97
0.90
Current Data ParametersNAME KV-V-862EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170508Time 11.21INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 291.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300052 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
200 180 160 140 120 100 80 60 40 20 ppm
40.97
55.37
76.84
77.16
77.48
79.87
111.50
114.39
114.86
119.11
120.04
121.58
122.79
126.21
128.95
131.29
136.62
159.00 Current Data Parameters
NAME KV-V-862EXPNO 3PROCNO 1
F2 - Acquisition ParametersDate_ 20170508Time 13.43INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 50.8DW 20.800 usecDE 6.00 usecTE 293.3 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127576 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S18
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
4.935
4.949
4.960
4.967
4.982
4.992
5.014
5.716
5.736
5.738
5.756
7.059
7.060
7.078
7.097
7.106
7.110
7.117
7.120
7.128
7.140
7.180
7.182
7.192
7.202
7.217
7.220
7.260
7.341
7.343
7.359
7.361
7.363
7.425
7.444
7.620
7.640
8.221
2.12
1.00
3.15
3.05
1.06
1.04
1.04
0.91
Current Data ParametersNAME KV-V-801EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170221Time 16.02INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 292.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
40.72
76.84
77.16
77.48
77.90
111.51
113.44
119.12
120.12
122.07
122.89
124.60
126.31
128.03
129.25
133.59
136.60
138.20 Current Data Parameters
NAME KV-V-801EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170222Time 13.28INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 50.8DW 20.800 usecDE 6.00 usecTE 293.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127588 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S19
9 8 7 6 5 4 3 2 1 ppm
0.000
4.781
4.802
4.813
4.834
4.913
4.932
4.945
4.964
5.042
5.061
5.081
6.912
6.917
7.005
7.024
7.071
7.090
7.105
7.110
7.123
7.142
7.159
7.176
7.196
7.253
7.273
7.289
7.308
7.327
7.347
7.374
7.378
7.382
8.068
0.99
1.00
0.98
0.96
1.00
2.10
1.19
1.04
1.01
1.00
0.98
0.94
Current Data ParametersNAME KV-VI-998EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20171124Time 16.02INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16
DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 128DW 60.800 usecDE 6.00 usecTE 294.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usec
PL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300453 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
406080100120140160180200 ppm
41.23
76.84
77.16
77.48
79.26
111.62
113.71
118.83
120.22
121.70
122.97
123.10
126.00
126.57
130.59
130.91
130.96
136.57
141.72 Current Data Parameters
NAME KV-VI-998EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20171124Time 16.08INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 389DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 295.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usec
PL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127596 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S20
9 8 7 6 5 4 3 2 1 ppm
0.072
4.882
4.904
4.914
4.935
5.031
5.050
5.062
5.081
5.135
5.155
5.175
7.021
7.027
7.068
7.087
7.106
7.196
7.204
7.209
7.213
7.225
7.231
7.260
7.364
7.385
7.387
7.389
7.410
7.437
7.458
8.158
1.06
1.00
0.98
0.93
1.03
3.11
2.09
1.83
0.84
Current Data ParametersNAME KV-V-821EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170313Time 12.15INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 292.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300052 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
41.14
76.84
77.16
77.48
79.31
111.61
113.96
118.91
120.23
121.66
123.00
125.99
129.63
129.78
132.19
136.62
138.37 Current Data Parameters
NAME KV-V-821EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170313Time 13.20INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 293.2 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127573 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S21
10 9 8 7 6 5 4 3 2 1 ppm
4.946
4.964
4.978
4.990
4.996
5.012
5.023
5.044
5.732
5.752
5.772
7.066
7.068
7.086
7.106
7.113
7.142
7.146
7.161
7.165
7.171
7.179
7.183
7.186
7.191
7.205
7.210
7.225
7.228
7.234
7.260
7.349
7.370
7.423
7.433
7.453
8.135
1.97
1.00
2.06
4.26
1.01
2.04
0.92
Current Data Parameters
NAME KV-VI-925
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170828
Time 12.44
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 2
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9846387 sec
RG 203
DW 60.800 usec
DE 6.00 usec
TE 294.2 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 11.42 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300050 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm
38.08
76.84
77.16
77.48
77.82
111.51
113.37
119.06
120.15
122.08
122.92
126.29
127.41
128.98
129.10
130.27
133.97
136.57 Current Data Parameters
NAME KV-VI-925
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170830
Time 12.26
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 512
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631988 sec
RG 57
DW 20.800 usec
DE 6.00 usec
TE 293.2 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.15 usec
PL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.90 dB
PL13 14.90 dB
PL2 -3.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127578 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S22
1234567891011 ppm
4.904
4.925
4.935
4.956
5.036
5.055
5.068
5.087
5.163
5.183
5.203
7.046
7.048
7.052
7.090
7.092
7.107
7.110
7.127
7.130
7.210
7.212
7.230
7.233
7.247
7.251
7.256
7.260
7.270
7.324
7.329
7.373
7.393
7.431
7.433
7.451
7.453
8.161
1.00
1.00
0.98
0.96
1.00
0.82
3.21
0.96
1.00
1.00
0.78
Current Data Parameters
NAME KV-V-868
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170713
Time 11.32
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 2
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9846387 sec
RG 228
DW 60.800 usec
DE 6.00 usec
TE 294.6 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 11.42 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300012 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
200 180 160 140 120 100 80 60 40 20 0 ppm
41.29
76.84
77.16
77.48
79.28
111.61
113.82
118.88
120.26
121.68
123.02
126.03
126.12
128.01
128.09
130.32
134.91
136.60
141.45 Current Data Parameters
NAME KV-V-868
EXPNO 6
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170717
Time 13.27
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 1024
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631988 sec
RG 57
DW 20.800 usec
DE 6.00 usec
TE 294.8 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.15 usec
PL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.90 dB
PL13 14.90 dB
PL2 -3.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127566 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S23
2345678910 ppm
1.181
4.797
4.818
4.828
4.849
4.945
4.964
4.977
4.995
5.064
5.084
5.104
6.927
6.932
6.986
6.988
7.005
7.023
7.025
7.111
7.113
7.131
7.149
7.151
7.172
7.175
7.193
7.202
7.218
7.224
7.273
7.293
7.309
7.329
8.076
1.00
1.00
0.98
1.00
1.03
1.08
4.19
2.05
0.77
Current Data ParametersNAME KV-V-798EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170221Time 15.51INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 161DW 60.800 usecDE 6.00 usecTE 293.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300389 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
30405060708090100110120130140150160170180 ppm
41.09
76.86
77.17
77.49
79.42
111.62
114.07
118.94
120.24
121.66
123.01
126.02
129.26
129.29
133.56
136.63
137.86 Current Data Parameters
NAME KV-V-798EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170223Time 14.51INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 293.1 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127556 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S24
11 10 9 8 7 6 5 4 3 2 1 ppm
4.880
4.901
4.911
4.932
5.034
5.053
5.066
5.084
5.161
5.181
5.201
6.989
6.994
7.014
7.016
7.027
7.032
7.073
7.075
7.091
7.093
7.111
7.113
7.197
7.200
7.218
7.220
7.235
7.238
7.260
7.286
7.292
7.299
7.304
7.308
7.316
7.321
7.354
7.375
7.402
7.403
7.422
7.423
8.137
1.00
1.00
0.98
2.82
0.99
1.01
2.00
1.03
0.98
0.84
Current Data ParametersNAME KV-VI-992-AEXPNO 3PROCNO 1
F2 - Acquisition ParametersDate_ 20171116Time 17.05INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16
DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 295.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usec
PL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
406080100120140160180 ppm
40.98
76.83
77.14
77.46
79.65
111.57
114.34
115.83
116.04
118.95
120.15
121.56
122.93
126.05
129.44
129.52
135.04
135.07
136.62
160.96
163.41 Current Data Parameters
NAME KV-VI-992-AEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20171116Time 12.31INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 409DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 64DW 20.800 usecDE 6.00 usecTE 295.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usec
PL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127592 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S25
14 13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
5.002
5.024
5.087
5.104
5.119
5.136
5.282
5.302
5.322
7.075
7.077
7.082
7.083
7.093
7.094
7.097
7.112
7.114
7.204
7.206
7.222
7.225
7.227
7.242
7.245
7.260
7.374
7.377
7.380
7.382
7.393
7.395
7.397
7.400
7.482
7.502
7.522
7.699
7.719
8.107
8.109
8.112
8.114
8.127
8.130
8.133
8.135
8.201
8.206
8.211
8.294
1.02
1.00
0.96
1.97
0.99
1.95
0.99
0.99
0.96
0.93
0.80
Current Data ParametersNAME KV-VI-996EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20171122Time 17.16INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536
SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 295.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
30405060708090100110120130140150160170 ppm
41.21
76.84
77.16
77.48
78.97
111.79
113.11
118.58
120.41
121.72
122.80
122.89
123.20
125.76
130.08
134.23
136.62
141.72
148.72 Current Data Parameters
NAME KV-VI-996EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20171122Time 19.11INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 2000DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 293.8 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usec
PL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127584 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S26
23456789 ppm
2.322
4.900
4.921
4.931
4.952
5.029
5.048
5.060
5.079
5.143
5.163
5.183
7.003
7.008
7.009
7.069
7.072
7.087
7.089
7.107
7.109
7.125
7.145
7.185
7.187
7.205
7.207
7.220
7.240
7.260
7.337
7.357
7.454
7.474
8.091
3.00
1.01
1.01
1.00
0.97
1.02
2.06
3.09
1.05
1.03
0.90
Current Data Parameters
NAME KV-VI-923
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170828
Time 12.52
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 2
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9846387 sec
RG 144
DW 60.800 usec
DE 6.00 usec
TE 294.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 11.42 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300050 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
200 180 160 140 120 100 80 60 40 20 ppm
21.17
41.31
76.84
77.16
77.48
79.75
111.49
114.69
119.06
120.02
121.66
122.75
126.22
127.73
129.71
136.25
136.59
137.32 Current Data Parameters
NAME KV-VI-923
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20170830
Time 16.06
INSTRUM spect
PROBHD 5 mm DUL 13C-1
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 423
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631988 sec
RG 64
DW 20.800 usec
DE 6.00 usec
TE 293.9 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.15 usec
PL1 0.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.90 dB
PL13 14.90 dB
PL2 -3.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127593 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S27
11 10 9 8 7 6 5 4 3 2 1 ppm
5.098
5.111
5.116
5.131
6.066
6.085
6.105
7.024
7.029
7.047
7.049
7.067
7.085
7.086
7.188
7.190
7.208
7.226
7.228
7.260
7.360
7.383
7.396
7.439
7.459
7.505
7.520
7.522
7.539
7.544
7.549
7.562
7.566
7.569
7.583
7.785
7.797
7.809
7.891
7.895
7.914
8.106
8.274
8.295
2.07
1.00
2.02
1.12
3.19
1.17
2.10
1.02
1.16
0.85
0.96
Current Data ParametersNAME KV-V-861EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170508Time 11.31INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 291.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========
NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
37.13
76.84
77.16
77.48
78.64
111.56
114.47
118.97
120.14
122.77
122.82
122.87
124.79
125.50
126.08
126.27
127.01
128.49
129.31
131.24
134.30
134.73
136.71 Current Data Parameters
NAME KV-V-861EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170508Time 12.17INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 795DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 292.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127557 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S28
234567891011 ppm
5.033
5.054
5.064
5.085
5.123
5.142
5.155
5.173
5.352
5.372
5.391
7.045
7.047
7.065
7.085
7.181
7.199
7.216
7.218
7.260
7.346
7.366
7.422
7.426
7.443
7.447
7.469
7.479
7.489
7.492
7.790
7.798
7.803
7.812
8.120
1.00
0.97
0.99
1.91
1.21
1.04
4.05
3.96
0.93
Current Data ParametersNAME KV-V-795EXPNO 3PROCNO 1
F2 - Acquisition ParametersDate_ 20170603Time 15.53INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 294.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300049 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
30405060708090100110120130140150160170 ppm
41.79
76.86
77.17
77.49
79.54
111.54
114.49
119.07
120.15
121.90
122.87
125.94
126.24
126.27
126.49
126.55
127.81
128.03
128.93
132.89
133.57
136.65
136.77 Current Data Parameters
NAME KV-V-795EXPNO 4PROCNO 1
F2 - Acquisition ParametersDate_ 20170603Time 17.29INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 596DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 64DW 20.800 usecDE 6.00 usecTE 296.7 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127557 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S29
9 8 7 6 5 4 3 2 1 ppm
0.070
4.902
4.920
4.933
4.951
5.036
5.056
5.067
5.088
5.238
5.258
5.277
6.163
6.171
6.307
6.312
6.315
6.319
7.120
7.142
7.149
7.156
7.209
7.227
7.246
7.260
7.377
7.387
7.390
7.397
7.554
7.574
8.157
0.97
1.00
0.97
0.89
0.88
2.09
0.99
1.91
0.96
0.83
Current Data ParametersNAME KV-V-855EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170424Time 17.14INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 256DW 60.800 usecDE 6.00 usecTE 293.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
35.84
76.84
77.16
77.48
78.00
107.52
110.60
111.66
111.76
118.84
120.21
122.79
122.84
125.82
136.44
142.39
152.31 Current Data Parameters
NAME KV-V-855EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170427Time 13.27INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 294.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127573 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S30
10 9 8 7 6 5 4 3 2 1 0 ppm
0.072
4.968
4.988
4.999
5.020
5.033
5.052
5.064
5.083
5.450
5.470
5.489
6.937
6.946
6.949
6.958
6.990
6.999
7.101
7.119
7.128
7.135
7.195
7.197
7.207
7.210
7.223
7.241
7.243
7.260
7.372
7.393
7.513
7.532
8.161
2.15
1.00
1.00
1.06
2.17
2.09
1.01
1.05
0.83
Current Data ParametersNAME KV-V-856EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170424Time 17.19INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 292.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
37.05
76.84
77.16
77.48
80.13
111.65
114.16
118.94
120.20
122.09
122.89
125.04
125.39
125.83
127.09
136.52
143.06 Current Data Parameters
NAME KV-V-856EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170503Time 21.18INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 64DW 20.800 usecDE 6.00 usecTE 293.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127590 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S31
11 10 9 8 7 6 5 4 3 2 1 ppm
3.773
4.911
4.932
4.942
4.963
5.024
5.043
5.055
5.074
5.121
5.141
5.161
6.842
6.848
6.863
6.869
6.999
7.005
7.230
7.231
7.239
7.252
7.260
7.266
7.269
7.275
7.282
7.295
7.305
7.311
7.319
7.325
7.332
7.339
7.353
8.041
3.00
1.12
1.13
1.08
2.16
1.01
1.92
3.85
0.93
Current Data ParametersNAME KV-V-836EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170324Time 10.29INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 292.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
405060708090100110120130140150160170 ppm
41.65
55.97
76.84
77.16
77.48
79.61
100.96
112.23
112.86
114.20
122.41
126.69
127.70
127.89
129.05
131.71
139.27
154.30 Current Data Parameters
NAME KV-V-836EXPNO 3PROCNO 1
F2 - Acquisition ParametersDate_ 20170328Time 18.44INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 401DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 64DW 20.800 usecDE 6.00 usecTE 294.3 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127568 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S32
3456789 ppm4.835
4.855
4.866
4.886
4.937
4.957
4.968
4.988
5.047
5.067
5.087
6.995
7.001
7.141
7.163
7.198
7.202
7.215
7.219
7.223
7.232
7.236
7.241
7.253
7.260
7.268
7.276
7.279
7.293
7.297
7.300
7.489
7.493
8.144
1.02
1.00
0.98
0.99
1.03
6.59
1.06
1.00
Current Data ParametersNAME KV-V-857EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20170428Time 9.56INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 161DW 60.800 usecDE 6.00 usecTE 293.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300281 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
41.41
76.84
77.16
77.48
79.52
112.99
113.35
114.12
121.57
122.87
125.77
127.78
127.89
127.97
129.18
135.21
138.81 Current Data Parameters
NAME KV-V-857EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20170428Time 10.13INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 276DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 294.1 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127580 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
S33
3. HPLC chromatogram of compounds, 3a-3s
S34
HPLC chromatogram of 3a
Data Graph
Minutes
20 21 22 23 24 25 26 27 28 29 30 31 32
Vo
lts
0.0
0.1
0.2
0.3
2
3.7
42
15374338
2
7.4
50
15493525
Detector A (215nm)744-2 racemic1 (70,30,H,IPA,0.9ml,OD-H) 744-2 racemic1 (70,30,H,IPA,0001.9ml,OD-H)
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 23.742 15374338 304685 49.81 MM 2 27.450 15493525 265447 50.19 MM
Totals 30867863 570132 100.00
S35
Data Graph
Minutes
22 23 24 25 26 27 28 29 30 31 32
Vo
lts
0.0
0.5
1.0
1.5
2
4.6
50
11890076
2
8.0
92
108322092
Detector A (215nm)764 (70,30,H,IPA,0.9ml,OD-H) 764 (70,30,H,IPA,0001.9ml,OD-H)
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 24.650 11890076 227370 9.89 MM 2 28.092 108322092 1709995 90.11 MM
Totals 120212168 1937365 100.00
S36
HPLC chromatogram of 3b
Data Graph
Minutes
10 11 12 13 14 15 16 17 18 19 20
Vo
lts
0.00
0.25
0.50
0.75
1.00
1.25
1
3.4
33
37751419
1
6.5
33
37848956
Detector A (215nm)KV-V- 772-2 OME RAC(70,30,H,IPA,0.9ml,OD-H) KV-V- 772-2 OME RAC(70,30,H,IPA,0001.9ml,OD-H)
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 13.433 37751419 1296054 49.94 MM 2 16.533 37848956 1032740 50.06 MM
Totals 75600375 2328794 100.00
S37
Data Graph
Minutes
10 11 12 13 14 15 16 17 18 19 20
Vo
lts
0.0
0.5
1.0
1.5
1
3.4
08
45463432
1
6.5
08
4664968
Detector A (215nm)KV-V- 788-2 OME(70,30,H,IPA,0.9ml,OD-H) KV-V- 788-2 OME(70,30,H,IPA,0001.9ml,OD-H) -H)
NameRetention TimeArea
Run Report
Detector A (215nm) Pk # Name Retention
Time Area Height Units Area
Percent Integration Codes
1 13.408 45463432 1575641 90.69 MM 2 16.508 4664968 132522 9.31 MM
Totals 50128400 1708163 100.00
S38
HPLC chromatogram of 3c
Data Graph
Minutes
20 22 24 26 28 30 32 34
Vo
lts
0.00
0.25
0.50
0.75
1.00
1.25
2
3.5
67
72
38
81
44
3
1.7
92
73
87
29
01
Detector A (215nm)KV-V--830- 3-methoxy rac(70,30,H,IPA,1ml,OD-H) KV-V--830- 3-methoxy rac(70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 23.567 72388144 1302427 49.49 MM 2 31.792 73872901 989913 50.51 MM
Totals 146261045 2292340 100.00
S39
Data Graph
Minutes
20 22 24 26 28 30 32 34
Vo
lts
0.0
0.5
1.0
1.5
2
3.5
58
87
40
08
1
3
1.7
75
10
46
08
52
8
Detector A (215nm)KV-V--825- 3-methoxy (70,30,H,IPA,1ml,OD-H) KV-V--825- 3-methoxy (70,30,H,IPA,1ml,OD-H) ) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 23.558 8740081 166035 7.71 MM 2 31.775 104608528 1353930 92.29 MM
Totals 113348609 1519965 100.00
S40
HPLC chromatogram of 3d
Data Graph
Minutes
22 23 24 25 26 27 28 29 30 31 32
Vo
lts
0.00
0.05
0.10
0.15
2
5.3
33
10433321
2
8.4
00
10460703
Detector A (215nm)KV-V- 778- 4 OME, RAC (70,30,H,IPA,1ml,OD-H) KV-V- 778- 4 OME, RAC (70,30,H,IPA,1ml,OD-H)001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 25.333 10433321 175432 49.93 MM 2 28.400 10460703 155170 50.07 MM
Totals 20894024 330602 100.00
S41
Data Graph
Minutes
22 23 24 25 26 27 28 29 30 31 32
Vo
lts
0.00
0.05
0.10
0.15
2
5.4
50
1958149
2
8.4
08
11091929
Detector A (215nm)KV-V- 790- 4 OME (70,30,H,IPA,1ml,OD-H) KV-V- 790- 4 OME (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 25.450 1958149 33525 15.00 MM 2 28.408 11091929 167495 85.00 MM
Totals 13050078 201020 100.00
S42
HPLC chromatogram of 3e
Data Graph
Minutes
16 18 20 22 24 26 28 30
Vo
lts
0.00
0.25
0.50
0.75
1.00
1.25
1
7.4
58
50950424
2
6.1
08
51631347
Detector A (215nm)KV-V- 804- 2-bromo rac (70,30,H,IPA,1ml,OD-H) KV-V- 804- 2-bromo rac (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
1 17.458 50950424 1266967 49.67 2 26.108 51631347 849369 50.33
Totals 102581771 2116336 100.00
S43
S44
Data Graph
Minutes
16 18 20 22 24 26 28 30
Vo
lts
0.0
0.5
1.0
1.5
2.0
2.5
1
7.3
58
105737673
2
6.1
92
4886257
Detector A (215nm)KV-V- 801- 2-bromo (70,30,H,IPA,1ml,OD-H) KV-V- 801- 2-bromo (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 17.358 105737673 2319452 95.58 MM 2 26.192 4886257 82789 4.42 MM
Totals 110623930 2402241 100.00
S45
HPLC chromatogram of 3e (Gram scale reaction)
Data Graph
Minutes
14 16 18 20 22 24 26 28 30 32
Vo
lts
0.0
0.1
0.2
0.3 1
7.1
33
11654233
2
8.0
75
265851
Detector A (220nm)KV-V1-1000-F1-2-br (70.30,H,IPA, 1ml, OD-H)KV-V1-1000-F1-2-br (70001.30,H,IPA, 1ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 17.133 11654233 304521 97.77 MM 2 28.075 265851 5333 2.23 MM
Totals 11920084 309854 100.00
S46
HPLC chromatogram of 3f
Data Graph
Minutes
22 24 26 28 30 32 34 36 38 40 42
Vo
lts
0.0
0.2
0.4
0.6
2
5.5
50
43048878
3
6.4
17
42904317
Detector A (220nm)KV-V1-3-BROMO RAC (70.30,H,IPA, 1 ml, OD-H)KV-V1-3-BROMO RAC (70001.30,H,IPA, 1 ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 25.550 43048878 715912 50.08 MM 2 36.417 42904317 492289 49.92 MM
Totals 85953195 1208201 100.00
S47
Data Graph
Minutes
22 24 26 28 30 32 34 36 38 40 42
Vo
lts
0.00
0.25
0.50
0.75
1.00
2
5.5
58
7088814
3
6.3
92
99041778
Detector A (220nm)KV-V1-998-3 BROMO RAC (70.30,H,IPA, 1 ml, OD-H)KV-V1-998-3 BROMO RAC (70001.30,H,IPA, 1 ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 25.558 7088814 124734 6.68 MM 2 36.392 99041778 1144285 93.32 MM
Totals 106130592 1269019 100.00
S48
HPLC chromatogram of 3g
Data Graph
Minutes
24 26 28 30 32 34 36 38 40
Vo
lts
0.0
0.2
0.4
0.6
0.8
1.0
2
8.6
00
69
68
51
19
3
5.3
67
69
94
66
27
Detector A (215nm)KV-V--829 (70,30,H,IPA,0.9ml,OD-H) KV-V--829 (70,30,H,IPA,0001.9ml,OD-H)
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 28.600 69685119 1023855 49.91 MM 2 35.367 69946627 817482 50.09 MM
Totals 139631746 1841337 100.00
S49
Data Graph
Minutes
24 26 28 30 32 34 36 38 40
Vo
lts
0.00
0.25
0.50
0.75
1.00
2
8.0
08
78
24
18
1
3
4.6
08
92
03
34
70
Detector A (215nm)KV-V--821- 4-bromo (70,30,H,IPA,1ml,OD-H) KV-V--821- 4-bromo (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 28.008 7824181 127636 7.84 MM 2 34.608 92033470 1094653 92.16 MM
Totals 99857651 1222289 100.00
S50
HPLC chromatogram of 3h
Data Graph
Minutes
16 18 20 22 24 26 28 30
Vo
lts
0.0
0.5
1.0
1.5
2.0 1
7.4
00
108109557
2
7.2
83
113373116
Detector A (220nm)KV-VI-926-2-CHLORO RAC (70,30,H,IPA,1.0 ml,OD-H)KV-VI-926-2-CHLORO RAC (70,30,H,IPA,1001.0 ml,OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 17.400 108109557 2303986 48.81 MM 2 27.283 113373116 1700283 51.19 MM
Totals 221482673 4004269 100.00
S51
Data Graph
Minutes
16 18 20 22 24 26 28 30
Vo
lts
0.0
0.5
1.0
1.5
1
7.4
83
64246146
2
7.6
08
3306390
Detector A (220nm)KV-VI-925-2-CHLORO (70,30,H,IPA,1.0 ml,OD-H)KV-VI-925-2-CHLORO (70,30,H,IPA,1001.0 ml,OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 17.483 64246146 1543635 95.11 MM 2 27.608 3306390 59164 4.89 MM
Totals 67552536 1602799 100.00
S52
HPLC chromatogram of 3i
Data Graph
Minutes
22 24 26 28 30 32 34 36
Vo
lts
0.0
0.2
0.4
0.6
2
4.2
58
25817844
3
1.3
67
25256125
Detector A (220nm)KV-V-865 3-chloro rac1 (70,30,H,IPA,1ml,OD-H)KV-V-865 3-chloro rac1 (70,30,H,IPA,1ml,OD-H)001
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 24.258 25817844 569362 50.55 MM 2 31.367 25256125 321903 49.45 MM
Totals 51073969 891265 100.00
S53
Data Graph
Minutes
22 24 26 28 30 32 34 36
Vo
lts
0.0
0.2
0.4
0.6 2
4.1
17
5423047
3
2.4
75
52427750
Detector A (220nm)KV-V-868 3-chloro (70,30,H,IPA,1ml,OD-H)KV-V-868 3-chloro (70,30,H,IPA,1ml,OD-H)001
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 24.117 5423047 93401 9.37 MM 2 32.475 52427750 695635 90.63 MM
Totals 57850797 789036 100.00
S54
HPLC chromatogram of 3j
Data Graph
Minutes
24 25 26 27 28 29 30 31 32 33 34 35 36
Vo
lts
0.00
0.05
0.10
0.15
0.20
0.25
2
6.1
58
7086150
3
1.9
08
6866023
Detector A (215nm)KV-V- 799- 4-chloro rac (70,30,H,IPA,1ml,OD-H) KV-V- 799- 4-chloro rac (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 26.158 7086150 121478 50.79 MM 2 31.908 6866023 96960 49.21 MM
Totals 13952173 218438 100.00
S55
Data Graph
Minutes
24 25 26 27 28 29 30 31 32 33 34 35 36
Vo
lts
0.0
0.5
1.0
1.5
2
6.0
42
9752378
3
1.2
58
107667620
Detector A (215nm)KV-V- 798- 4-chloro (70,30,H,IPA,1ml,OD-H) KV-V- 798- 4-chloro (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 26.042 9752378 173109 8.31 MM 2 31.258 107667620 1413574 91.69 MM
Totals 117419998 1586683 100.00
S56
HPLC chromatogram of 3k
Data Graph
Minutes
20 22 24 26 28 30 32 34
Vo
lts
0.0
0.5
1.0
1.5
2.0
2
2.9
25
142411922
2
9.3
92
140326599
Detector A (220nm)KV-V1-990 4-F RAC (70.30,H,IPA, 1 ml, OD-H)KV-V1-990 4-F RAC (70001.30,H,IPA, 1 ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 22.925 142411922 2268586 50.37 MM 2 29.392 140326599 1977432 49.63 MM
Totals 282738521 4246018 100.00
S57
Data Graph
Minutes
20 22 24 26 28 30 32 34
Vo
lts
0.0
0.5
1.0
1.5
2
3.1
25
12311510
2
9.3
50
132618809
Detector A (220nm)KV-V1-992 4-F (70.30,H,IPA, 1 ml, OD-H)KV-V1-992 4-F (70001.30,H,IPA, 1 ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 23.125 12311510 247683 8.49 MM 2 29.350 132618809 1801035 91.51 MM
Totals 144930319 2048718 100.00
S58
HPLC chromatogram of 3l
Data Graph
Minutes
48 50 52 54 56 58 60 62 64 66 68 70
Vo
lts
0.0
0.1
0.2
0.3
5
1.9
25
50780931
6
2.6
08
50662404
Detector A (220nm)KV-V1-989-3 NITRO RAC (70.30,H,IPA, 1 ml, OD-H)KV-V1-989-3 NITRO RAC (70001.30,H,IPA, 1 ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 51.925 50780931 272925 50.06 MM 2 62.608 50662404 321747 49.94 MM
Totals 101443335 594672 100.00
S59
Data Graph
Minutes
50 52 54 56 58 60 62 64 66 68 70
Vo
lts
0.0
0.1
0.2
0.3
0.4
5
4.4
67
6029578
6
2.0
00
66528404
Detector A (220nm)KV-V1-996-3 NITRO (70.30,H,IPA, 1 ml, OD-H)KV-V1-996-3 NITRO (70001.30,H,IPA, 1 ml, OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 54.467 6029578 45836 8.31 MM 2 62.000 66528404 409924 91.69 MM
Totals 72557982 455760 100.00
S60
HPLC chromatogram of 3m
Data Graph
Minutes
16 17 18 19 20 21 22 23 24 25
Vo
lts
0.0
0.5
1.0
1.5
2.0
2.5
1
8.4
50
122305181
2
1.4
42
126846417
Detector A (220nm)KV-VI-924-4-METHYL RAC 70,30,H,IPA,1.0 ml,OD-H)KV-VI-924-4-METHYL RAC 70,30,H,IPA,1001.0 ml,OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 18.450 122305181 2498915 49.09 MM 2 21.442 126846417 2334296 50.91 MM
Totals 249151598 4833211 100.00
S61
Data Graph
Minutes
16 17 18 19 20 21 22 23 24 25
Vo
lts
0.0
0.2
0.4
0.6
1
8.7
25
4535525
2
1.7
33
32111946
Detector A (220nm)KV-VI-923-4-METHYL 1 (70,30,H,IPA,1.0 ml,OD-H)KV-VI-923-4-METHYL 1 (70,30,H,IPA,1001.0 ml,OD-H)
NameRetention TimeArea
Run Report Detector A (220nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 18.725 4535525 111354 12.38 MM 2 21.733 32111946 642779 87.62 MM
Totals 36647471 754133 100.00
S62
HPLC chromatogram of 3n
Data Graph
Minutes
20 22 24 26 28 30 32 34 36 38 40
Vo
lts
0.00
0.25
0.50
0.75
1.00
1.25
2
3.0
58
75394238
3
3.8
75
76150824
Detector A (215nm)KV-V- 810- 1 NAPH, RAC (70,30,H,IPA,1ml,OD-H) KV-V- 810- 1 NAPH, RAC (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 23.058 75394238 1260431 49.75 MM 2 33.875 76150824 858235 50.25 MM
Totals 151545062 2118666 100.00
S63
Data Graph
Minutes
20 22 24 26 28 30 32 34 36 38 40
Vo
lts
0.0
0.5
1.0
1.5
2
3.2
92
70125984
3
4.3
25
10052546
Detector A (215nm)KV-V- 807- 1 NAPH (70,30,H,IPA,1ml,OD-H) KV-V- 807- 1 NAPH (70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 23.292 70125984 1429080 87.46 MM 2 34.325 10052546 121711 12.54 MM
Totals 80178530 1550791 100.00
S64
HPLC chromatogram of 3o
Data Graph
Minutes
30 35 40 45 50 55 60 65
Vo
lts
0.0
0.1
0.2
0.3
0.4
3
7.0
58
38629796
5
9.0
25
38674445
Detector A (215nm)KV-V- 791- 2 NAPH ,RAC (70,30,H,IPA,0.9ml,OD-H) KV-V- 791- 2 NAPH ,RAC (70,30,H,IPA,0001.9ml,OD-H)
NameRetention TimeArea
Run Report
Detector A (215nm) Pk # Name Retention
Time Area Height Units Area
Percent Integration Codes
1 37.058 38629796 433422 49.97 MM 2 59.025 38674445 266509 50.03 MM
Totals 77304241 699931 100.00
S65
Data Graph
Minutes
35.0 37.5 40.0 42.5 45.0 47.5 50.0 52.5 55.0 57.5 60.0 62.5 65.0
Vo
lts
0.0
0.1
0.2
0.3
0.4
0.5
3
7.0
42
9062660
5
8.9
33
66503739
Detector A (215nm)KV-V- 795- 2 NAPH (70,30,H,IPA,0.9ml,OD-H) KV-V- 795- 2 NAPH (70,30,H,IPA,0001.9ml,OD-H)
NameRetention TimeArea
Run Report
Detector A (215nm) Pk # Name Retention
Time Area Height Units Area
Percent Integration Codes
1 37.042 9062660 102566 11.99 MM 2 58.933 66503739 458084 88.01 MM
Totals 75566399 560650 100.00
S66
HPLC chromatogram of 3p
Data Graph
Minutes
12 14 16 18 20 22 24
Vo
lts
0.0
0.5
1.0
1.5
1
4.9
25
46758246
2
1.7
67
49011649
Detector A (215nm)KV-V-775 -2 furan rac 2 I(70,30,H,IPA,1ml,OD-H) KV-V-775 -2 furan rac 2 I(70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 14.925 46758246 1475570 48.82 MM 2 21.767 49011649 1030372 51.18 MM
Totals 95769895 2505942 100.00
S67
Data Graph
Minutes
12 14 16 18 20 22 24
Vo
lts
0.0
0.5
1.0
1.5
2.0
1
4.9
33
66095708
2
1.9
08
14777257
Detector A (215nm)KV-V-855 -furan 2 (70,30,H,IPA,1ml,OD-H) KV-V-855 -furan 2 (70,30,H,IPA,1ml,OD-H) 002
NameRetention TimeArea
Run Report
Detector A (215nm) Pk # Name Retention
Time Area Height Units Area
Percent Integration Codes
1 14.933 66095708 1984981 81.73 MM 2 21.908 14777257 315032 18.27 MM
Totals 80872965 2300013 100.00
S68
HPLC chromatogram of 3q
Data Graph
Minutes
20 21 22 23 24 25 26 27 28 29 30
Vo
lts
-0.75
-0.50
-0.25
0.00
0.25
0.50
2
2.2
50
22471889
2
6.1
08
22296069
Detector A (215nm)KV-V-786 -2 thiophene racI(70,30,H,IPA,1ml,OD-H) KV-V-786 -2 thiophene racI(70,30,H,IPA,1ml,OD-H)001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 22.250 22471889 467786 50.20 MM 2 26.108 22296069 392018 49.80 MM
Totals 44767958 859804 100.00
S69
Data Graph
Minutes
20 21 22 23 24 25 26 27 28 29 30
Vo
lts
0.0
0.5
1.0
1.5
2.0
2.5
2
2.0
83
121202197
2
6.1
08
28658130
Detector A (215nm)KV-V-856 -2 thiophene I(70,30,H,IPA,1ml,OD-H) KV-V-856 -2 thiophene I(70,30,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 22.083 121202197 2285854 80.88 MM 2 26.108 28658130 501563 19.12 MM
Totals 149860327 2787417 100.00
S70
HPLC chromatogram of 3r
Data Graph
Minutes
26 28 30 32 34 36 38 40 42
Vo
lts
-0.2
0.0
0.2
0.4
2
8.6
33
21
59
85
87
3
7.7
67
20
67
76
52
Detector A (215nm)KV-V--836- 5-methoxy indole rac (85,15,H,IPA,1ml,OD-H) KV-V--836- 5-methoxy indole rac (85,15,H,IPA,1ml,OD-H)001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 28.633 21598587 369081 51.09 MM 2 37.767 20677652 267605 48.91 MM
Totals 42276239 636686 100.00
S71
Data Graph
Minutes
26 28 30 32 34 36 38 40 42
Vo
lts
0.0
0.2
0.4
0.6
0.8
2
8.2
33
45
46
72
58
3
7.8
17
61
86
06
2
Detector A (215nm)KV-V--833- 5-methoxy indole (85,15,H,IPA,1ml,OD-H) KV-V--833- 5-methoxy indole (85,15,H,IPA,1ml,OD-H) 001
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 28.233 45467258 727072 88.02 MM 2 37.817 6186062 82632 11.98 MM
Totals 51653320 809704 100.00
S72
HPLC chromatogram of 3s
Data Graph
Minutes
16 18 20 22 24 26 28 30
Vo
lts
0.00
0.25
0.50
0.75
1.00
1.25
1
7.2
75
42430703
2
6.2
33
41688078
Detector A (215nm)KV-V-835 -5- bromo indole rac3 (70,30,H,IPA,0.7ml,OD-H) KV-V-835 -5- bromo indole rac3 (70,30,H,IPA,0001.7ml,OD-H)
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 17.275 42430703 1164735 50.44 MM 2 26.233 41688078 768726 49.56 MM
Totals 84118781 1933461 100.00
S73
Data Graph
Minutes
16 18 20 22 24 26 28 30
Vo
lts
0.0
0.5
1.0
1.5
2.0
1
7.3
50
71071268
2
5.4
92
8564704
Detector A (215nm)KV-V-857 -5- bromo indole (70,30,H,IPA,0.7ml,OD-H) KV-V-857 -5- bromo indole (70,30,H,IPA,0001.7ml,OD-H)
NameRetention TimeArea
Run Report Detector A (215nm)
Pk # Name Retention Time
Area Height Units Area Percent
Integration Codes
1 17.350 71071268 2033264 89.25 MM 2 25.492 8564704 166981 10.75 MM
Totals 79635972 2200245 100.00
S74
Comparison of observed and reported optical rotations for 3a-3s
S.
No
Compound Reported
[α]DT
Observed
[α]DT
Reported Observed
Retention time
tR
ee (%) Retention time
tR
ee (%)
1 3aa
[α]D20
= -23.9 [α]D28
= -15.0 tminor = 19.2 min
tmajor = 23.7 min
1.0 ml/min
96%ee
tminor = 24.6 min
tmajor = 28.0 min,
0.9 ml/min
80%ee
2 3ba
[α]D20
= -47.8 [α]D26
= -28.6 tmajor = 16.1 min
tminor = 18.0 min,
0.8 ml/min
95%ee tmajor = 13.4 min
tminor = 16.5 min,
0.9 ml/min
81%ee
3 3ca
[α]D20
= -16.4 [α]D32
= -10.0 tminor = 49.5 min,
tmajor = 70.6 min,
0.5 ml/min
97%ee tminor = 23.5 min,
tmajor = 31.7 min,
1.0 ml/min
84%ee
4 3da
[α]D20
= -28.2 [α]D26
= -11.2 tminor = 31.0 min
tmajor = 35.7 min,
0.8 ml/min
95%ee tminor = 25.4 min
tmajor = 28.4 min,
1.0 ml/min
70%ee
5 3ea [α]D
28 = -79.9 tmajor = 17.3 min,
tminor = 26.1 min
91%ee
6 3fa [α]D
20 = -16.0 [α]D
30 = -13.1 tminor = 21.4 min
tmajor = 30.3 min,
1.0 ml/min
95%ee tminor = 25.5 min
tmajor = 36.3 min,
1.0 ml/min
83%ee
7 3ga [α]D
20= +1.8 [α]D
25= +0.9 tminor = 23.3 min
tmajor = 30.5 min,
1.0 ml/min
95%ee tminor = 28.0 min
tmajor = 34.6 min,
1.0 ml/min
84%ee
8 3ha
[α]D20
= -50.0 [α]D25
= -58.4 tmajor = 14.3min
tminor = 22.7 min,
1.0 ml/min
72%ee tmajor = 17.5 min
tminor = 27.6 min,
1.0 ml/min
90%ee
9 3ib
[α]D20
= -18.1 [α]D31
= -14.2 tminor =21.7 min
tmajor = 19.6 min,
1.0 ml/min
92%ee tminor = 24.1min,
tmajor = 32.4 min,
1.0 ml/min
81%ee
10 3ja
[α]D20
= -7.1 [α]D30
= -5.4 tminor = 22.2 min
tmajor = 28.5 min,
1.0 ml/min
95%ee tminor = 26.0 min
tmajor = 31.2 min
1.0 ml/min
83%ee
11 3ka
[α]D20
= -35.0 [α]D30
= -19.3 tminor = 19.5 min,
tmajor = 25.1 min,
95%ee tminor = 23.1 min,
tmajor = 29.7 min,
83%ee
S75
1.0 ml/min 1.0 ml/min
12 3la [α]D
20 = -14.8 [α]D
30 = -8.3 tminor = 36.3 min,
tmajor = 50.1 min
94%ee tminor = 54.5 min,
tmajor = 62.0 min,
1.0 ml/min
83%ee
13 3ma [α]D
20 = -13.3 [α]D
26 = -8.0 tminor = 15.6 min,
tmajor = 18.8 min
93%ee tminor = 18.7 min,
tmajor = 21.7 min,
1.0 ml/min
85%ee
14 3na [α]D
20 = -25.8 [α]D
25 = -13.7 tmajor = 31.1 min
tminor = 39.7 min,
0.8 ml/min
94%ee tmajor = 23.2 min
tminor = 34.3 min,
1.0 ml/min
75%ee
15 3oa [α]D
20 = -3.5 [α]D
30 = -2.1 tminor = 48.8 min
tmajor = 61.3 min,
0.8 ml/min
95%ee tminor = 37.0 min
tmajor = 58.9 min,
0.9 ml/min
76%ee
16 3pa [α]D
20 = +38.2 [α]D
32 = +10.0 tmajor = 18.6 min,
tminor = 26.1 min,
0.8 ml/min
95%ee tmajor = 14.9 min,
tminor = 21.9 min,
1.0 ml/min
63%ee
17 3qa [α]D
30 = -25.3 [α]D
25 = -32.0 tmajor = 27.3 min,
tminor = 31.7 min,
0.8 ml/min
92%ee tmajor = 22.0 min,
tminor = 26.1 min,
1.0 ml/min
61%ee
18 3ra [α]D
30 = +30.2 [α]D
30 = +15.7 tmajor = 16.6 min
tminor = 19.6 min,
0.8 ml/min
96%ee tmajor = 28.2 min
tminor = 37.8 min,
1.0 ml/min
76%ee
19 3sa [α]D
30 = +41.0 [α]D
31 = +18.4 tmajor = 15.7 min,
tminor = 20.4 min,
0.8 ml/min
93%ee tmajor = 17.3 min,
tminor = 25.4 min,
0.7 ml/min
78%ee
a HPLC (Daicel Chiralcel OD-H, hexane/2-propanol = 70:30, b HPLC (Daicel Chiralpak AD-H, hexane/2-
propanol = 90:10
S76
Optimized coordinates and Energies of CRCB TETHERED BIPYRIDINE-Zn--NITROSTYRENE COMPLEX I are given below (in Hartrees): Sum of electronic and zero-point Energies = -2842.571443
Sum of electronic and thermal Energies = -2842.515336
Sum of electronic and thermal Enthalpies = -2842.514391
Sum of electronic and thermal Free Energies = -2842.671105
C -0.67822200 -3.72332000 -0.57301400
C -2.66316100 -2.49196900 -0.15419200
C -3.44265400 -3.61333000 -0.43264900
C -2.81453800 -4.81068700 -0.80748200
C -1.43380000 -4.86999400 -0.87565900
H -4.52190300 -3.55352900 -0.37591000
H -3.41031800 -5.68670700 -1.04449500
H -0.94354800 -5.78857100 -1.17359400
N -1.31152700 -2.55200800 -0.24321100
C -5.06319200 -0.99897400 -1.51406700
C -3.77837800 -0.34902700 -1.04987700
C -5.62944800 -0.35252000 0.76932300
C -6.08217800 -0.96569700 -0.54489000
C -4.11089700 1.04445900 -0.53562500
C -5.08396800 1.03279800 0.47776000
H -6.41074400 -0.34357500 1.53031100
H -3.00916800 -0.32924000 -1.82665500
C -4.41239700 -1.21265800 1.26781100
H -4.75800600 -2.24698900 1.37777900
C -3.25312600 -1.14568400 0.21843300
H -2.44812400 -0.54643800 0.64665500
C -4.00380100 -0.77813800 2.67615700
O -4.78118900 -0.33749800 3.49729800
O -2.69170500 -0.97330400 2.90133000
C -2.15128900 -0.50799300 4.16461700
H -1.14327300 -0.17264200 3.91290200
H -2.74664200 0.34308700 4.50164000
C -2.15075500 -1.62267700 5.19820400
C -3.48326600 2.23121700 -0.90092400
C -3.85931200 3.42398000 -0.27191700
C -4.84322300 3.41770400 0.71872600
C -5.45520300 2.21920500 1.10440600
H -2.69071900 2.23042200 -1.64371700
H -3.36722600 4.35219000 -0.54523600
H -5.12690600 4.34741800 1.20378400
H -6.20380800 2.20921500 1.89178500
C -7.58496400 -2.04531800 -2.09161300
C -7.34248200 -1.48185700 -0.83244000
C -5.29631200 -1.59291200 -2.75202300
C -6.55841900 -2.13013200 -3.03360600
H -8.56943000 -2.44072500 -2.32512900
H -8.13354900 -1.43977700 -0.08790800
S77
H -4.50484100 -1.63352500 -3.49632200
H -6.74736700 -2.58545300 -4.00165700
H -3.17299600 -1.92847900 5.43687800
H -1.59684000 -2.49421100 4.83603500
H -1.67414200 -1.27345500 6.12032100
C 0.78589500 -3.70370400 -0.59299100
C 2.74294700 -2.36438500 -0.50596900
C 3.54880900 -3.49266300 -0.64281300
C 2.94720400 -4.75588100 -0.74963900
C 1.56775400 -4.86448700 -0.72874500
H 4.62691300 -3.39428500 -0.64768400
H 3.56236700 -5.64537900 -0.84390100
H 1.09858900 -5.83801700 -0.79803900
N 1.39289300 -2.48069400 -0.46678800
C 4.99335600 -1.42751000 1.45560700
C 3.71506900 -0.66707200 1.16214100
C 5.67186500 -0.00472500 -0.40899400
C 6.04984900 -1.07591000 0.59594300
C 4.02690500 0.81738800 1.19483400
C 5.09498300 1.17592000 0.35685300
H 6.49802900 0.28271700 -1.06065500
H 2.89940000 -0.93112600 1.84082600
C 4.50310600 -0.60999800 -1.26608900
H 4.88173600 -1.52017900 -1.74568900
C 3.29335100 -0.96246900 -0.33860900
H 2.48344100 -0.26939700 -0.57181900
C 4.14490500 0.32421400 -2.42221800
O 4.92724000 1.09786000 -2.93362500
O 2.87271300 0.15087400 -2.82384200
C 2.37040600 1.03570500 -3.85840900
H 1.31515900 1.16115000 -3.60894800
H 2.88303600 1.99578300 -3.77016800
C 2.57115500 0.42880000 -5.23775700
C 3.33150400 1.78896300 1.90932000
C 3.73265900 3.12570800 1.80883100
C 4.81625900 3.47896900 1.00230200
C 5.49352600 2.50580200 0.25903800
H 2.47412700 1.51086500 2.51620600
H 3.19541000 3.89267300 2.35854300
H 5.12008800 4.51929100 0.93125700
H 6.31237600 2.78365800 -0.39846100
C 7.46926400 -2.68957100 1.69326400
C 7.28231200 -1.71484300 0.70490800
C 5.18328500 -2.39004100 2.44333100
C 6.43097200 -3.01301500 2.56824900
H 8.43260900 -3.18235200 1.78938800
H 8.09600400 -1.45109300 0.03378900
H 4.36954300 -2.65260300 3.11484100
H 6.58683700 -3.75917600 3.34223000
H 3.63602800 0.32634100 -5.46317600
H 2.09853900 -0.55582500 -5.30627200
S78
H 2.12164000 1.07749000 -5.99705100
Zn 0.02241200 -0.95696500 -0.09250900
O -0.17061600 0.51780800 1.26877800
O 0.19272900 0.87399400 -0.92986000
N -0.01375500 1.43139200 0.27970600
C -0.10583900 2.74592100 0.48805900
H -0.32288600 2.97932100 1.52299900
C 0.05360900 3.70782000 -0.49308600
H 0.31816800 3.36075200 -1.48628200
C -0.08803300 5.12681000 -0.29891300
C 0.18733600 6.00600500 -1.37863300
C -0.49504400 5.72849700 0.92189400
C 0.07598300 7.38470100 -1.24628400
H 0.49908600 5.57980000 -2.32927100
C -0.60110000 7.10821100 1.04847300
H -0.73794500 5.10325300 1.77624000
C -0.31713600 7.95388500 -0.03030200
H 0.29876700 8.02320100 -2.09769500
H -0.91475700 7.53205900 1.99951400
H -0.40460000 9.03118300 0.07417300