supplementary material synthesis of (+)-l-733,060, (+)-cp ... · 7 210 200 190 180 170 160 150 140...
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Supplementary Material
Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-Hydroxypipecolic Acid:
Application of an Organocatalytic Direct Vinylogous Aldol Reaction
Sunil V. Pansare* and Eldho K. Paul
Department of Chemistry Memorial University
St. John’s, NL, Canada A1B 3X7 1H and 13C spectra..................................................................................................................2-34 HPLC traces...........................................................................................................................35-37
1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
2
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3473D/1EKP-03-90B(CDCl3)
1.02
1.01
1.01
1.00
6.13
0.00
1.55
2.29
2.30
5.08
5.09
5.10
5.18
5.18
5.18
5.19
5.19
5.19
6.18
6.18
6.19
6.19
7.26
7.34
7.35
7.35
7.36
7.36
7.37
7.37
7.37
7.38
7.39
7.39
7.40
7.41
7.41
7.42
7.42
7.42
7.43
7.43
7.44
OHOO
Ph
CDCl3, 500 MHz1 (anti)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
3
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-03-90B
73.0
976
.64
77.0
677
.49
86.6
1
123.
2312
6.06
128.
5612
8.79
138.
28
152.
85
173.
05
OHOO
Ph
CDCl3, 75 MHz1 (anti)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
4
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3421D/1EKP-03-38C(CDCl3)
1.03
1.03
1.02
1.00
1.02
5.59
-0.0
0
1.61
2.77
2.78
4.70
4.72
5.15
5.16
5.16
5.17
5.17
5.17
6.12
6.12
6.13
6.13
7.16
7.17
7.17
7.18
7.26
7.31
7.31
7.32
7.34
7.35
7.35
7.36
7.36
7.36
7.37
7.37
7.38
7.38
7.39
7.40
7.40
7.40
7.40
7.41
7.41
7.42
OHOO
Ph
CDCl3, 500 MHz1 (syn)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
5
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-03-38B
-0.0
0
75.7
276
.60
77.0
277
.44
86.8
5
123.
0112
6.72
128.
8012
9.01
137.
66
153.
00
172.
40
OHOO
Ph
CDCl3, 75 MHz1 (syn)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
6
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3554A/1EKP-04-41A(CDCl3)
0.27
1.06
1.39
1.94
1.24
1.00
5.74
-0.0
01.
921.
931.
931.
941.
942.
262.
272.
282.
282.
292.
302.
422.
442.
452.
452.
462.
462.
472.
472.
522.
532.
542.
552.
562.
57
4.68
4.68
4.69
4.69
4.70
4.70
4.70
4.71
4.72
5.12
5.13
7.26
7.30
7.31
7.31
7.32
7.32
7.33
7.33
7.34
7.36
7.37
7.38
7.38
7.39
OHOO
Ph
CDCl3, 500 MHz
1aanti (major) + syn (minor)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
7
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-41AEKP-04-41A(CDCl3) 0.
00
20.6
824
.02
28.4
828
.59
73.4
476
.60
77.0
277
.44
83.2
483
.41
126.
0212
6.95
128.
1312
8.64
128.
7312
8.75
138.
3113
8.39
176.
8317
7.61
OHOO
Ph
CDCl3, 75 MHz
1aanti (major) + syn (minor)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
8
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3602A/1EKP-04-57A(CDCl3)
2.16
2.42
0.38
3.01
1.12
0.12
1.00
6.29
0.00
2.22
2.22
2.23
2.24
2.25
2.25
2.27
2.40
2.41
2.44
2.45
2.45
2.47
2.47
2.49
2.49
2.50
2.51
2.52
2.89
2.91
4.82
4.83
4.83
4.84
4.84
4.84
4.85
4.86
5.51
5.53
5.72
5.73
7.26
7.42
7.42
7.43
7.43
7.43
OSO2CH3OO
Ph
CDCl3, 500 MHz
1banti (major) + syn (minor)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
9
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-57A
0.00
22.0
924
.22
27.7
427
.91
38.9
739
.27
76.6
177
.04
77.4
680
.31
80.3
882
.81
84.3
4
126.
8512
7.53
129.
1412
9.18
129.
6212
9.98
133.
4613
3.70
175.
9817
6.07
OSO2CH3OO
Ph
CDCl3, 75 MHz
1banti (major) + syn (minor)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
10
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3735C/1EKP-05-28A(CDCl3)
2.34
0.23
2.31
1.00
1.12
0.12
6.18
-0.0
01.
981.
981.
981.
992.
002.
002.
002.
002.
012.
012.
012.
022.
022.
032.
042.
052.
062.
072.
072.
082.
082.
082.
092.
092.
092.
102.
102.
112.
112.
112.
122.
352.
362.
372.
382.
382.
392.
392.
402.
402.
402.
412.
412.
412.
422.
432.
432.
432.
442.
452.
462.
462.
484.
594.
604.
674.
684.
684.
694.
694.
714.
894.
907.
277.
357.
367.
367.
377.
377.
397.
407.
407.
407.
417.
417.
427.
427.
437.
44
N3OO
Ph
CDCl3, 500 MHz
2syn (major) + anti (minor)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
11
-0.0
0
22.3
024
.62
28.0
028
.10
67.5
668
.45
76.5
977
.01
77.4
381
.19
81.4
0
127.
2112
7.80
128.
9612
9.10
129.
1212
9.26
134.
5113
4.60
176.
1717
6.38
N3OO
Ph
CDCl3, 75 MHz
2syn (major) + anti (minor)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
12
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3622A/1EKP-04-45C(CDCl3)
0.99
1.06
1.01
1.02
1.02
1.00
1.00
0.96
3.05
2.05
-0.0
0
1.68
2.01
2.02
2.13
2.13
2.14
2.14
2.15
2.37
2.38
2.40
2.41
2.41
2.42
2.70
2.71
2.72
4.08
4.67
4.67
5.85
7.27
7.33
7.35
7.35
7.36
7.37
7.41
7.42
7.42
7.43
7.44
CDCl3, 500 MHz
NH
OH
PhO
cis 3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
13
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-45CEKP-04-45C -0
.00
26.0
626
.68
61.8
7
66.2
3
76.6
177
.03
77.4
6
127.
0312
8.68
129.
15
137.
85
172.
28
CDCl3, 75 MHz
NH
OH
PhO
cis 3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
14
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3552B/1EKP-04-32C(CDCl3)
0.98
1.04
1.05
1.02
1.01
1.00
1.00
0.96
3.04
1.98
0.00
1.46
1.46
1.47
1.47
1.61
2.05
2.16
2.16
2.17
2.17
2.18
2.40
2.43
2.44
2.44
2.45
2.72
2.73
2.74
2.76
4.09
4.10
4.10
4.69
4.70
5.70
7.26
7.35
7.36
7.36
7.38
7.39
7.39
7.40
7.43
7.43
7.44
7.44
7.44
7.45
7.46
CDCl3, 500 MHz
NH
OH
PhO
trans 3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
15
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-32CEKP-04-32C -0
.00
26.0
526
.68
61.9
3
66.2
8
76.5
977
.01
77.4
4
126.
9812
8.77
129.
23
137.
80
172.
13
CDCl3, 75 MHz
NH
OH
PhO
trans 3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
16
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3572A/1EKP-04-47A(CDCl3)
1.10
1.42
1.70
1.59
1.05
1.00
1.01
1.02
1.81
4.02
0.00
1.49
1.51
1.52
1.70
1.70
1.71
1.71
1.87
1.89
2.02
2.02
2.02
2.03
2.04
2.05
2.05
2.81
2.81
2.83
2.83
3.19
3.19
3.20
3.78
3.78
3.86
3.86
7.25
7.25
7.26
7.26
7.27
7.27
7.28
7.32
7.34
7.34
7.35
7.36
CDCl3, 500 MHz
NH
OH
Ph
3a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
17
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-47AEKP-04-47A(CDCl3) 0.
00
19.9
0
31.9
8
47.4
6
65.0
2
68.9
2
76.5
977
.01
77.4
4
126.
5912
7.27
128.
45
142.
02
CDCl3, 75 MHz
NH
OH
Ph
3a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
18
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3591B/1EKP-04-51B(CDCl3)
9.29
1.08
1.11
3.13
1.02
1.02
1.04
1.00
1.86
2.00
2.02
0.00
1.37
1.58
1.66
1.67
1.68
1.70
1.70
1.72
1.77
1.77
1.78
1.78
1.80
1.81
1.83
1.83
1.84
1.84
3.01
3.01
3.03
3.04
3.06
3.07
3.98
3.99
4.00
4.01
4.01
4.02
4.03
4.07
4.08
4.09
4.10
4.11
5.31
5.33
7.26
7.26
7.28
7.32
7.32
7.33
7.33
7.35
7.44
7.46
7.46
CDCl3, 500 MHz4
N
OH
Ph
O OtBu
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-51BEKP-04-51B -0
.00
23.0
727
.70
28.3
2
39.4
5
59.2
5
70.0
5
76.5
977
.01
77.4
479
.89
127.
1912
8.37
138.
43
155.
39
CDCl3, 75 MHz4
N
OH
Ph
O OtBu
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
20
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3591A/1EKP-04-52D(CDCl3)
CDCl3, 500 MHz
N
O
Ph
O OtBu
CF3
CF3
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
21
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-52DEKP-04-52D -0
.00
24.1
825
.85
28.4
0
39.2
4
55.4
4
69.1
5
76.5
977
.01
77.4
478
.69
80.1
3
117.
8712
1.33
121.
3812
1.43
121.
4812
5.09
127.
0712
7.15
127.
2112
8.29
128.
3312
8.70
130.
9513
1.39
131.
8313
2.28
137.
9914
1.00
155.
29
CDCl3, 75 MHz
N
O
Ph
O OtBu
CF3
CF3
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
22
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3594A/1EKP-04-53A(CDCl3)
1.08
1.20
1.06
1.20
1.03
1.01
1.00
1.03
1.01
1.00
1.00
1.86
2.00
2.00
1.97
0.98
-0.0
01.
521.
541.
541.
701.
701.
711.
711.
731.
731.
741.
771.
771.
861.
89
2.20
2.20
2.21
2.84
2.85
2.87
3.27
3.28
3.28
3.68
3.68
3.84
3.85
4.12
4.15
4.51
4.53
7.25
7.25
7.26
7.28
7.28
7.30
7.32
7.33
7.36
7.37
7.38
7.44
7.69
CDCl3, 500 MHz
NH
O
Ph
CF3
CF3
(+)-L-773,060
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
23
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-53B
0.00
20.2
8
28.3
5
46.9
4
64.1
6
70.0
776
.61
77.0
477
.11
77.4
6
121.
1912
1.24
121.
2912
1.48
125.
0912
6.81
127.
2812
7.45
127.
5012
8.20
130.
6613
1.10
131.
5413
1.98
141.
1214
1.38
CDCl3, 75 MHz
NH
O
Ph
CF3
CF3
(+)-L-773,060
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
24
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3608A/1EKP-04-62B(CDCl3)
9.30
2.06
2.05
1.00
0.98
0.92
2.02
0.85
2.02
-0.0
01.
371.
391.
431.
451.
491.
641.
901.
911.
921.
931.
941.
951.
961.
971.
97
2.44
2.45
2.45
2.46
3.30
3.30
3.31
3.32
3.33
3.34
3.35
4.08
5.66
7.20
7.22
7.26
7.28
7.30
7.34
7.36
7.37
CDCl3, 500 MHz
N
O
Ph
O OtBu5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
25
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-62BEKP-04-62B -0
.00
22.8
7
28.2
8
37.3
440
.15
66.3
4
76.6
177
.03
77.4
580
.76
125.
4012
7.63
128.
94
135.
61
155.
01
205.
51
CDCl3, 75 MHz
N
O
Ph
O OtBu5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
26
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3735B/1EKP-05-24D(CDCl3)
9.64
2.07
2.31
1.07
1.09
1.05
0.93
1.05
1.00
1.21
2.12
2.03
0.00
1.36
1.37
1.48
1.65
1.66
1.67
1.67
1.68
1.69
1.77
1.78
1.79
1.86
1.87
1.88
3.14
3.16
3.19
3.21
3.99
3.99
4.00
4.02
4.03
5.19
5.20
7.25
7.26
7.27
7.28
7.28
7.28
7.30
7.30
7.31
7.32
7.33
7.33
7.43
7.43
7.44
7.44
CDCl3, 500 MHz
N Ph
O OtBu
NH2
6
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
27
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3630A/1EKP-04-72C(CDCl3)
9.11
1.36
1.22
3.04
0.95
1.00
2.99
2.03
0.98
0.87
0.94
0.98
3.67
2.09
1.90
-0.0
0
1.41
1.42
1.52
1.54
1.62
1.63
1.63
1.76
1.76
1.78
1.78
1.81
1.82
2.96
2.96
3.04
3.04
3.05
3.06
3.06
3.71
3.79
3.82
3.85
3.87
3.94
3.96
5.47
6.80
6.80
6.82
6.87
6.89
6.90
7.19
7.20
7.20
7.21
7.21
7.21
7.22
7.25
7.25
7.26
7.26
7.26
7.26
7.29
7.30
7.31
7.31
7.31
7.32
7.33
7.57
7.59
CDCl3, 500 MHz6a
N
HN
PhOCH3
O OtBu
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
28
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-72CEKP-04-72C -0
.00
24.3
626
.80
28.4
3
39.5
1
46.6
1
55.0
657
.26
76.5
977
.01
77.4
479
.60
110.
13
120.
3912
6.89
128.
0612
8.09
129.
2212
9.53
139.
19
155.
2715
7.54
CDCl3, 75 MHz6a
N
HN
PhOCH3
O OtBu
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
29
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3634A/1EKP-04-74A(CDCl3)
1.04
1.14
2.02
1.15
1.00
1.94
1.01
0.94
2.92
1.04
1.00
0.92
0.96
0.97
0.94
5.11
0.00
1.38
1.40
1.57
1.59
1.60
1.60
1.60
1.62
1.77
1.90
1.91
1.92
1.93
1.94
1.95
2.12
2.81
2.81
2.82
2.82
3.25
3.25
3.26
3.26
3.27
3.28
3.28
3.28
3.39
3.42
3.44
3.45
3.65
3.68
3.87
6.66
6.68
6.78
6.79
6.80
6.80
6.81
6.96
6.98
7.12
7.14
7.16
7.20
7.20
7.21
7.21
7.23
7.25
7.25
7.25
7.26
7.26
7.27
7.28
7.29
7.29
7.30
CDCl3, 500 MHz
NH
HN
PhOCH3
(+)-CP-99,994
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
30
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-04-74A
20.3
8
28.2
4
46.7
747
.81
54.7
254
.78
64.0
0
76.6
577
.07
77.5
0
109.
81
119.
9812
6.33
126.
5612
7.82
128.
1612
8.30
129.
61
142.
49
157.
62
CDCl3, 75 MHz
NH
HN
PhOCH3
(+)-CP-99,994
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
31
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-3770D/1EKP-05-35B(CDCl3)
2.77
4.42
2.37
0.30
1.00
1.00
0.30
1.34
0.31
1.00
6.08
0.67
0.00
1.80
1.81
1.82
1.83
1.84
1.84
1.84
1.85
1.85
1.86
2.01
2.02
2.02
2.03
2.03
2.04
2.04
2.09
2.11
2.12
2.13
2.13
2.14
2.15
2.15
2.16
2.16
2.17
2.74
2.74
2.75
2.77
2.78
3.13
3.14
3.15
3.16
3.16
3.17
3.18
3.19
3.80
3.81
3.83
3.84
4.35
4.36
4.38
4.39
5.21
5.22
5.22
5.23
5.24
5.25
5.25
5.54
5.55
5.98
5.99
7.26
7.28
7.29
7.30
7.31
7.31
7.33
7.34
7.34
7.35
7.36
7.37
7.37
7.39
7.41
7.42
7.42
7.48
7.49
CDCl3, 500 MHz
N Ph
O CF3
O
O
CH3
8 (rotamers)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
32
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-05-35B
0.00
21.0
521
.13
23.4
723
.85
24.9
4
38.8
241
.08
41.1
341
.18
41.2
3
55.5
357
.67
70.5
772
.39
76.6
577
.07
77.4
9
110.
8611
4.67
118.
4812
2.30
127.
7612
7.97
128.
0212
8.74
128.
9013
5.04
135.
38
155.
7715
6.25
156.
7215
7.20
169.
6316
9.71
CDCl3, 75 MHz
N Ph
O CF3
O
O
CH3
8 (rotamers)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
33
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
EKP-05-46B3-Hydroxy pipecolic acid
2.08
2.03
1.02
1.00
0.99
1.00
1.63
1.64
1.66
1.69
1.69
1.70
1.71
1.72
1.75
1.76
1.77
1.88
1.89
1.90
1.91
1.92
1.93
1.94
1.95
1.96
1.97
2.89
2.93
2.94
2.97
2.99
3.32
3.33
3.33
3.36
3.37
3.38
3.60
3.61
4.44
4.72
D2O, 500 MHz
NH
OH
COOH
(2S,3R)-3-Hydroxypipecolic acid
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
34
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
EKP-05-46B3-Hydroxy pipecolic acid 15
.88
28.7
0
43.5
7
62.2
464
.10
172.
28
D2O, 75 MHz
NH
OH
COOH
(2S,3R)-3-Hydroxypipecolic acid
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
35
AD-H 99 hex 1ipa 210nm 90 min
Time5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00
AU
0.0
1.0e-1
2.0e-1
3.0e-1
4.0e-1
5.0e-1
6.0e-1
7.0e-1
8.0e-1
9.0e-1
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
EKP-05-65A Sm (SG, 20x4) Diode Array Range: 1.855
AreaArea%
1.9595.332.73
Area26052.82
1275896.0036516.55
Height42958
185287848598
Time26.2833.9935.75
33.991275896
26.2826053
35.7536517
5
N
O
Ph
O OtBu
minor
major
N
O
Ph
O OtBu
5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
36
AD-H 99 hex 1ipa 210nm 60 min
Time5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00 50.00
AU
0.0
1.0e-1
2.0e-1
3.0e-1
4.0e-1
5.0e-1
6.0e-1
7.0e-1
8.0e-1
9.0e-1
1.0
1.1
1.2
1.3
1.4
EKP-05-25B (Recemic) Sm (SG, 20x4) Diode Array Range: 1.546
AreaArea%
0.5352.6346.84
Area10471.55
1035272.94921369.69
Height23461
15356661273964
Time12.6734.7036.25
34.701035273
12.6710472
36.25921370
Recemic
N
O
Ph
O OtBu
N
O
Ph
O OtBu
5 racemic
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
37
OD-H 90 hex 10ipa 210nm 60 min
Time2.00 4.00 6.00 8.00 10.00 12.00 14.00 16.00 18.00
AU
0.0
1.0e-1
2.0e-1
3.0e-1
4.0e-1
5.0e-1
6.0e-1
7.0e-1
8.0e-1
9.0e-1
1.0
1.1
EKP-05-72A(3rd run) Sm (SG, 20x4) Diode Array Range: 1.211
AreaArea%
1.071.44
94.782.71
Area5400.147273.15
478479.5913663.85
Height2136239599
120636930785
Time3.624.926.279.75
6.27478480
4.9272733.62
54009.75
13664
NH
HN
PhOCH3
(+)-CP-99,994
minor
major
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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