kazuhiro yoshida1tmco.chem.chiba-u.jp/members/研究業績リストga.pdf · 2020. 12. 25. ·...
TRANSCRIPT
KAZUHIRO YOSHIDA
ORIGINAL PAPERS
85
Enantioselective Desymmetrization of 1,3-Disubstituted Adamantane Derivatives via Rhodium-Catalyzed C–H Bond Amination: Access to Optically Active Amino Acids
Containing Adamantane Core Risa Yasue and Kazuhiro Yoshida*
Adv. Synth. Catal. 2021, 363, 1662-1671.
84
Oxidative Cyclization of o-(1-Hydroxy-2-alkynyl)-N-tosylanilides for Synthesis of 4-Quinolones
Jun-ichi Ueda, Yuuki Enomoto, Mizuki Seki, Takuma Konishi, Masamichi Ogasawara,* and Kazuhiro Yoshida*
J. Org. Chem. 2020, 85, 6420-6428.
iPrO2C R
+ Rh2(S-TCPTTL)4 (catalyst)
Me
tBu
NH2SO2O
iPrO2CNHSO2O
R
Me
tBu
H H
H
up to 85% ee
desymmetrizationHOOC
H2NR
H
chiralbuilding blocks
deprotection
amino acids
N
O
RNH
OH
R
Ts Ts
or MnO2, DMF
8 examplesR’ ’R
Intramolecular Hydroamination/Cyclization
MnO2, TBAI, CHCl3
83
Development of Planar Chiral Five-membered Cyclic (Amino)(ferrocenylene)carbene Ligand and Its Iridium Dicarbonyl Complex
Waka Takagaki, Risa Yasue, and Kazuhiro Yoshida* Bull. Chem. Soc. Jpn. 2020, 92, 200-204.
82
Synthesis of [1]Benzothiopheno[2,3-b][1]benzothiophene Derivatives through Iodine-mediated Sulfuration Reaction of 1,1-Diarylethylenes
Shuta Sakai, Kazuki Sato, and Kazuhiro Yoshida* Tetrahedron Lett. 2020, 61, 151476
81
Versatile and Enantioselective Preparation of Planar-Chiral Metallocene-Fused 4-Dialkylaminopyridines and Their Application in Asymmetric Organocatalysis
Kazuhiro Yoshida,* Qiang Liu, Risa Yasue, Shiro Wada, Ryosuke Kimura, Takuma Konishi, and Masamichi Ogasawara* ACS Catal. 2020, 10, 292-301
Tolman electronic parameter (TEP) = 2048 cm-1
IrCl
OC COFe
NMes
PhPh
Fe
NMesPh Ph
OO
MeO
FeH
S
SSS8 (4 equiv)I2 (1 equiv)
S8 (4 equiv)I2 (4 equiv)
toluene, reflux, 4 h toluene, reflux, 24 h
O
OH
OMe
H
Fe
R'5
CHO
Fe
R'5
NHTs
(S)-11b-d
MgBr
(S)-2b-d
2) MnO2, TBAI
1)
R' = Me, Ph, Bn
Fe
R'5
N
NR2
(S)-1
Me3SiNR2TiCl4
(S)-14b-d
Fe
R'5
NHTs
O
single enantiomers
iodide-catalyzedcyclization
NR2 = NMe2, pyrroridylNEt2, morpholyl
Fe
R'5
NTs
O
(–)-3b-d
80
Chiral Bicyclic NHC/Cu Complexes for Catalytic Asymmetric Borylation of a,b-Unsaturated Esters
Yuya Miwa, Takumi Kamimura, Kiyoaki Sato, Daichi Shishido, and Kazuhiro Yoshida* J. Org. Chem. 2019, 84, 14291-14296
79
Synthesis and Application of Planar Chiral Cyclic (Amino)(ferrocenyl)carbene Ligands Bearing FeCp* Group
Risa Yasue and Kazuhiro Yoshida* Organometallics 2019, 38, 2211-2217
78
Planar-Chiral Ferrocene-Based N-Heterocyclic Carbene Ligands Kazuhiro Yoshida* and Risa Yasue
Chem. Eur. J. 2018, 24, 18575-18586
N NMes
Ph
CuClR1O
O
R2
R1O
O
R2
OH
up to 85% ee(Bpin)2
+NaBO3(5 mol %)
77
Coordination Behavior of a Planar Chiral Cyclic (Amino)(Ferrocenyl)Carbene Ligand in Iridium Complexes
Yuta Shikata, Risa Yasue, and Kazuhiro Yoshida* Chem. Eur. J. 2017, 23, 16806-16812
76
A Planar Chiral Six-Membered Cyclic (Amino)(Ferrocenyl)Carbene and Its Sulfur Adduct
Risa Yasue, Masaru Miyauchi, and Kazuhiro Yoshida* Tetrahedron: Asymmetry 2017, 28, 824-829
75
Synthesis of o-Allyloxy(ethynyl)benzene Derivatives by Cu-Catalyzed Suzuki–Miyaura-Type Reaction and Their Transformations into Heterocyclic
Compounds Kohei Watanabe, Takashi Mino,* Eri Ishikawa, Miyu Okano, Tatsuya Ikematsu, Yasushi
Yoshida, Masami Sakamoto, Kazuki Sato, and Kazuhiro Yoshida Eur. J. Org. Chem. 2017, 2359-2368
Graphical Abstract
NFe
NFe
LiHMDS S
I
74
Planar Chiral Cyclic (Amino)(ferrocenyl)carbene as Ligand for Transition Metals Risa Yasue, Masaru Miyauchi, and Kazuhiro Yoshida*
Adv. Synth. Catal. 2017, 359, 255-259
73
Enantioselective Synthesis of Ferrocene- or Cymantrene-Fused Planar-Chiral Phospholes Hao Hu, Wei-Yi Wu, Tamotsu Takahashi, Kazuhiro Yoshida, and Masamichi Ogasawara*
Eur. J. Inorg. Chem. 2017, 325-329
72
Enantioselective Nitroso Aldol Reaction Catalyzed by Chiral Phosphine-Silver Complex Akira Yanagisawa,* Yuqin Lin, Akihiro Takeishi, and Kazuhiro Yoshida
Eur. J. Org. Chem. 2016, 5355-5359
71
Enantio- and Diastereoselective Cross-Annulation of Enal and Ketone with New Chiral Bicyclic N-Heterocyclic Carbene Catalysts
Momo Hasegawa, Kazuhiro Yoshida,* and Akira Yanagisawa* Chem. Lett. 2016, 45 294-296
70
Catalytic Enantioselective Synthesis of Chiral 3-Amino-2-oxindoles by a Mannich Approach
Akira Yanagisawa,* Naoyuki Kushihara, Takuya Sugita, Moe Horiguchi, Kazuki Ida, and Kazuhiro Yoshida
Synlett 2015, 26 2541-2546
69
Chiral Bicyclic NHC/Ir Complexes for Catalytic Asymmetric Transfer Hydrogenation of Ketones
Kazuhiro Yoshida,* Takumi Kamimura, Hiroshi Kuwabara, and Akira Yanagisawa* Chem. Commun. 2015, 51, 15442-15445
N
N
R
R'
IrCl
Ir complex 8dz (0.01 mol%)
R = 2,4,6-tricyclohexylphenylR' = bis(4-(trifluoromethyl)phenyl)methyl
Me
O
Me
OH
t-BuOK (0.1 mol%)i-PrOH, 70 °C, 1 h 97% ee
4,500 h-1 TOF
68
Utilization of Optically Active Secondary Phosphine–Boranes: Synthesis of P-chiral Diphosphines and Their Enantioinduction Ability in Rhodium-catalyzed Asymmetric
Hydrogenation Tsuneo Imamoto,* Yumi Horiuchi, Eri Hamanishi, Satoshi Takeshita, Ken Tamura, Masashi
Sugiya, and Kazuhiro Yoshida Tetrahedron 2015, 71, 6471-6480
67
Enantioselective Synthesis of Planar-Chiral Ferrocene-Fused 4-Pyridones and Their Application in Construction of Pyridine-Based Organocatalyst Library
Masamichi Ogasawara,* Shiro Wada, Erika Isshiki, Takumi Kamimura, Akira Yanagisawa,* Tamotsu Takahashi,* and Kazuhiro Yoshida*
Org. Lett. 2015, 17, 2286-2289
66
Reactive Barium-Promoted Benzylation of Diaryl Azo Compounds Akira Yanagisawa,* Toshiki Sawae, Seiya Yamafuji, Toshihiko Heima, and Kazuhiro Yoshida
Synlett 2015, 26 1073-1076
65
Asymmetric Aldol Reaction Catalyzed by a Chiral Phosphine–Silver Complex Akira Yanagisawa,* Ryoji Miyake, and Kazuhiro Yoshida
Eur. J. Org. Chem 2014, 4248-4253
64
Synthesis of Substituted Styrenes and 3-Vinylphenols Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
Kazuhiro Yoshida,* Kana Nishii, Yuto Kano, Shiro Wada, and Akira Yanagisawa* J. Org. Chem 2014, 79, 4231-4239
63
Catalytic Enantioselective Mannich-Type Reaction via a Chiral Silver Enolate Akira Yanagisawa,* Yuqin Lin, Ryoji Miyake, and Kazuhiro Yoshida
Org. Lett. 2014, 16, 86-89
62
Asymmetric a-Amination Reaction of Alkenyl Trifluoroacetates Catalyzed by Chiral Phosphine-Silver Complex
Akira Yanagisawa,* Ryoji Miyake, and Kazuhiro Yoshida Org. Biomol. Chem. 2014, 12, 1935-1941
61
Enantioselective Protonation of Alkenyl Trifluoroacetates Catalyzed by Chiral Tin Methoxide: A New Entry to Optically Active Ketones
Akira Yanagisawa,* Takuya Sugita, and Kazuhiro Yoshida Chem. Eur. J. 2013, 19, 16200-16203
60
Synthesis of 4-Vinylindoles Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis Kazushi Hayashi, Kazuhiro Yoshida,* and Akira Yanagisawa*
J. Org. Chem 2013, 78, 3464-3469
59
α-Selective Allylation of Azo Compounds Using Allylic Barium Reagents Akira Yanagisawa,* Takuya Jitsukawa, and Kazuhiro Yoshida
Synlett 2013, 24, 635-639
58
Development of Asymmetric Reactions Catalyzed by Chiral Organotin-Alkoxide Reagents
Akira Yanagisawa* and Kazuhiro Yoshida Chem. Rec. 2013, 13, 117-127
57
Catalytic Enantioselective Synthesis of Chiral Isatin Derivatives by an Aldol Approach Akira Yanagisawa,* Naoyuki Kushihara, Takuya Sugita, and Kazuhiro Yoshida
Synlett. 2012, 1783-1788
56
Catalytic Enantioselective N-Nitroso Aldol Reaction of γ,δ-Unsaturated δ-Lactones Akira Yanagisawa,* Takeo Fujinami, Yu Oyokawa, Takuya Sugita, and Kazuhiro Yoshida
Org. Lett. 2012, 14, 2434-2437
55
Rigid P-Chiral Phosphine Ligands with tert-Butylmethylphosphino Groups for Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes
Tsuneo Imamoto,* Ken Tamura, Zhenfeng Zhang, Yumi Horiuchi, Masashi Sugiya, Kazuhiro Yoshida, Akira Yanagisawa, and Ilya D. Gridnev*
J. Am. Chem. Soc. 2012, 134, 1754-1769
54
Catalytic Asymmetric Cycloaddition Reaction of Alkenyl Trichloroacetates with Nitrones Akira Yanagisawa,* Atsuto Izumiseki, Takuya Sugita, Naoyuki Kushihara, and Kazuhiro
Yoshida Synlett. 2012, 107-112
53
Recent Advances in Selective Reactions Promoted by Barium Reagents Akira Yanagisawa* and Kazuhiro Yoshida
Synlett. 2011, 2929-2938
52
Construction of Carbocyclic Ring of Indoles Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Kazushi Hayashi, and Akira Yanagisawa* Org. Lett. 2011, 13, 4762-4765
51
Asymmetric Addition of Diethylzinc to Aldehydes Catalyzed by New Zinc-amides Prepared by a Rhodium-catalyzed Asymmetric Addition
Kazuhiro Yoshida,* Naohisa Akashi, and Akira Yanagisawa* Tetrahedron: Asymmetry 2011, 22, 1225-1230
RCM
N NR2
R3
R5
R6R2
R3 R5
R6
R4
R1 R1R7OH
R4
R7NR2
R3 R5
R6
R1
R4
HO R7 H2O
PhCHOEt2Zn (40 equiv.)
Ph
OH
hexane, 30 °C, 24 h(20 equiv.)
dioxane, 50 °C, 3 h
[RhCl(C2H4)2]2 (3 mol % Rh)(R,R)-Ph-Bod* (6 mol %)Me2Zn (1.5 equiv.)
Ar H
NTs
Ar Me
NTsMeZn
82% yield86% ee
Ar = 2,3-(MeO)2C6H3
50
Catalytic Enantioselective Synthesis of Chiral γ-Butyrolactones Akira Yanagisawa,* Naoyuki Kushihara, and Kazuhiro Yoshida
Org. Lett. 2011, 13, 1576-1578
49
Ring Size-Selective Ring-Closing Olefin Metathesis: Taking Advantage of the Deleterious Effect of Ethylene Gas
Kazuhiro Yoshida,* Yuto Kano, Hidetoshi Takahashi, and Akira Yanagisawa* Adv. Synth. Catal. 2011, 353, 1229-1233
48
Synthesis of Biaryl Compounds Using Tandem Ruthenium-Catalyzed Ring-Closing Metathesis
Kazuhiro Yoshida,* Hiroaki Shida, Hidetoshi Takahashi, and Akira Yanagisawa* Chem. Eur. J. 2011, 17, 344-349
Grubbs 2nd
NTs30 °C, 2 h
nNTs NTs(1 mol %)Grubbs 2nd
30 °C, 2 h
(1 mol %)
>99%91%
96%15%
(n = 2) (n = 3)
under N2 (1 atm)under C2H4 (1 atm)
[Ru]
HO
OH
[Ru]
OH
OH
OH
OH
RCEM RCM
2 H2O
47
Enantiopure 1,2-Bis(tert-butylmethylphosphino)benzene as a Highly Efficient Ligand in Rhodium-Catalyzed Asymmetric Hydrogenation
Ken Tamura, Masashi Sugiya, Kazuhiro Yoshida, Akira Yanagisawa, and Tsuneo Imamoto* Org. Lett. 2010, 12, 4400-4403
46
Dibutyltin Dimethoxide-Catalyzed Cyano Transfer to Aldehydes and Imines Akira Yanagisawa,* Takuya Matsumoto, Naoyuki Kushihara, and Kazuhiro Yoshida
Adv. Synth. Catal. 2010, 352, 2918-2922
45
Selective Propargylation of Azo Compounds with Barium Reagents Akira Yanagisawa,* Takanori Koide, and Kazuhiro Yoshida
Synlett. 2010, 1515-1518
52-92%
44
Bicyclic Imidazoles for Modular Synthesis of Chiral Imidazolium Salts Kazuhiro Yoshida,* Shingo Horiuchi, Tomoko Takeichi, Hiroaki Shida, Tsuneo Imamoto, and
Akira Yanagisawa* Org. Lett. 2010, 12, 1764-1767
43
Enantioselective Nitroso Aldol Reaction Catalyzed by QuinoxP*·Silver(I) Complex and Tin Methoxide
Akira Yanagisawa,* Satoshi Takeshita, Youhei Izumi, and Kazuhiro Yoshida J. Am. Chem. Soc. 2010, 132, 5328-5329
42
Catalytic Asymmetric Three-Component Mannich-Type Reaction of Alkenyl Trichloroacetates
Atsuto Izumiseki, Kazuhiro Yoshida, and Akira Yanagisawa* Org. Lett. 2009, 11, 5310-5313
N N
X
RR'
X = O or CH2
N N
X
R
R' = alkyl
chiral module
orN
NX
R
N
NX
R
41
Methanol-Assisted Catalysis by Chiral Tin Methoxides: An Alternative Asymmetric Aldol Process
Akira Yanagisawa,* Tomoya Satou, Atsuto Izumiseki, Youichi Tanaka, Masahiko Miyagi, Takayoshi Arai, and Kazuhiro Yoshida Chem. Eur. J. 2009, 15, 11450-11453
40
Asymmetric Aldol Reaction of Ketones with Alkenyl Trichloroacetates Catalyzed by Dibutyltin Dimethoxide and BINAP·Silver(I) Complex: Construction of a Chiral
Tertiary Carbon Center Akira Yanagisawa,* Yuuki Terajima, Kazuma Sugita, and Kazuhiro Yoshida
Adv. Synth. Catal. 2009, 351, 1757-1762
39
Optically Active Dinuclear Palladium Complexes Containing a Pd–Pd Bond: Preparation and Enantioinduction Ability in Asymmetric Ring Opening Reactions
Tomokazu Ogura, Kazuhiro Yoshida, Akira Yanagisawa, and Tsuneo Imamoto* Org. Lett. 2009, 11, 2245-2248
41 Methanol-Assisted Catalysis by Chiral Tin Methoxides: An Alternative Asymmetric
Aldol Process Akira Yanagisawa,* Tomoya Satou, Atsuto Izumiseki, Youichi Tanaka, Masahiko Miyagi,
Takayoshi Arai, and Kazuhiro Yoshida Chem. Eur. J. 2009, 15, 11450-11453
40 Asymmetric Aldol Reaction of Ketones with Alkenyl Trichloroacetates Catalyzed by
Dibutyltin Dimethoxide and BINAP·Silver(I) Complex: Construction of a Chiral Tertiary Carbon Center
Akira Yanagisawa,* Yuuki Terajima, Kazuma Sugita, and Kazuhiro Yoshida Adv. Synth. Catal. 2009, 351, 1757-1762
39 Optically Active Dinuclear Palladium Complexes Containing a Pd–Pd Bond: Preparation
and Enantioinduction Ability in Asymmetric Ring Opening Reactions Tomokazu Ogura, Kazuhiro Yoshida, Akira Yanagisawa, and Tsuneo Imamoto*
Org. Lett. 2009, 11, 2245-2248
Pd Pd
PP
P P
X XMe
t-BuMe
t-Bu
t-Bu Me
Me t-Bu
1a: X = Cl1b: X = Br1c: X = I
Me2Zn (2 equiv)1c (3 mol %)AgOTf (6.6 mol %)
N
NHR2
R2
R1
R1
R1
R1
up to 99% ee
38
Synthesis of Carbocyclic Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
Hidetoshi Takahashi, Kazuhiro Yoshida,* and Akira Yanagisawa* J. Org. Chem. 2009, 74, 3632-3640
37
Rapid Screening for Asymmetric Catalysts: the Efficient Connection of Two Different Catalytic Asymmetric Reactions
Kazuhiro Yoshida,* Takeharu Toyoshima, Naohisa Akashi, Tsuneo Imamoto, and Akira Yanagisawa*
Chem. Commun. 2009, 2923-2925
36
Dibutyltin Dibromide-catalyzed Trimethylsilylcyanation of Aldehydes and Imines Akira Yanagisawa,* Takuya Matsumoto, Takayoshi Arai, and Kazuhiro Yoshida
Chem. Lett. 2009, 38, 336-337
38 Synthesis of Carbocyclic Aromatic Compounds Using Ruthenium-Catalyzed
Ring-Closing Enyne Metathesis Hidetoshi Takahashi, Kazuhiro Yoshida,* and Akira Yanagisawa*
J. Org. Chem. 2009, 74, 3632-3640
OH
orCHO
X
M
++H
37 Rapid Screening for Asymmetric Catalysts: the Efficient Connection of Two Different
Catalytic Asymmetric Reactions Kazuhiro Yoshida,* Takeharu Toyoshima, Naohisa Akashi, Tsuneo Imamoto, and Akira
Yanagisawa* Chem. Commun. 2009, 2923-2925
A
C
Asymmetric Catalyst 1*B*
Asymmetric Catalyst 2* D*
�
36 Dibutyltin Dibromide-catalyzed Trimethylsilylcyanation of Aldehydes and Imines
Akira Yanagisawa,* Takuya Matsumoto, Takayoshi Arai, and Kazuhiro Yoshida Chem. Lett. 2009, 38, 336-337
38 Synthesis of Carbocyclic Aromatic Compounds Using Ruthenium-Catalyzed
Ring-Closing Enyne Metathesis Hidetoshi Takahashi, Kazuhiro Yoshida,* and Akira Yanagisawa*
J. Org. Chem. 2009, 74, 3632-3640
OH
orCHO
X
M
++H
37 Rapid Screening for Asymmetric Catalysts: the Efficient Connection of Two Different
Catalytic Asymmetric Reactions Kazuhiro Yoshida,* Takeharu Toyoshima, Naohisa Akashi, Tsuneo Imamoto, and Akira
Yanagisawa* Chem. Commun. 2009, 2923-2925
A
C
Asymmetric Catalyst 1*B*
Asymmetric Catalyst 2* D*
�
36 Dibutyltin Dibromide-catalyzed Trimethylsilylcyanation of Aldehydes and Imines
Akira Yanagisawa,* Takuya Matsumoto, Takayoshi Arai, and Kazuhiro Yoshida Chem. Lett. 2009, 38, 336-337
35
Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Fumihiro Kawagoe, Kazushi Hayashi, Shingo Horiuchi, Tsuneo Imamoto,* and Akira Yanagisawa*
Org. Lett. 2009, 11, 515-518
34
Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin Metathesis, Dehydration, Oxidation, and Tautomerization
Kazuhiro Yoshida,* Takeharu Toyoshima, and Tsuneo Imamoto* Bull. Chem. Soc. Jpn. 2008, 81, 1512-1517
33
Synthesis of Substituted Phenols by Using the Ring-Closing Metathesis/Isoaromatization Approach
Kazuhiro Yoshida,* Rintaro Narui, and Tsuneo Imamoto* Chem. Eur. J. 2008, 14, 9706-9713
35 Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin
Metathesis Kazuhiro Yoshida,* Fumihiro Kawagoe, Kazushi Hayashi, Shingo Horiuchi, Tsuneo Imamoto,*
and Akira Yanagisawa* Org. Lett. 2009, 11, 515-518
RCMN
R2
R3
R4R5
N
OR2 R1
R3R4
R5
54
OR1
N
OHR2 R1
R4R5
6
34 Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin
Metathesis, Dehydration, Oxidation, and Tautomerization Kazuhiro Yoshida,* Takeharu Toyoshima, and Tsuneo Imamoto*
Bull. Chem. Soc. Jpn. 2008, 81, 1512-1517
OH
HO RCM
OH
HO
OH OH
HOoror
DehydrationOxidationTautomerization
33 Synthesis of Substituted Phenols by Using the Ring-Closing Metathesis/Isoaromatization
Approach Kazuhiro Yoshida,* Rintaro Narui, and Tsuneo Imamoto*
Chem. Eur. J. 2008, 14, 9706-9713
OR1
R3
R4R5
R2O
R1
R3R4
R5R2
2 3
OHR1
R3R4
R5R2
4
RCM isoaromatization
35 Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin
Metathesis Kazuhiro Yoshida,* Fumihiro Kawagoe, Kazushi Hayashi, Shingo Horiuchi, Tsuneo Imamoto,*
and Akira Yanagisawa* Org. Lett. 2009, 11, 515-518
RCMN
R2
R3
R4R5
N
OR2 R1
R3R4
R5
54
OR1
N
OHR2 R1
R4R5
6
34 Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin
Metathesis, Dehydration, Oxidation, and Tautomerization Kazuhiro Yoshida,* Takeharu Toyoshima, and Tsuneo Imamoto*
Bull. Chem. Soc. Jpn. 2008, 81, 1512-1517
OH
HO RCM
OH
HO
OH OH
HOoror
DehydrationOxidationTautomerization
33 Synthesis of Substituted Phenols by Using the Ring-Closing Metathesis/Isoaromatization
Approach Kazuhiro Yoshida,* Rintaro Narui, and Tsuneo Imamoto*
Chem. Eur. J. 2008, 14, 9706-9713
OR1
R3
R4R5
R2O
R1
R3R4
R5R2
2 3
OHR1
R3R4
R5R2
4
RCM isoaromatization
35 Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin
Metathesis Kazuhiro Yoshida,* Fumihiro Kawagoe, Kazushi Hayashi, Shingo Horiuchi, Tsuneo Imamoto,*
and Akira Yanagisawa* Org. Lett. 2009, 11, 515-518
RCMN
R2
R3
R4R5
N
OR2 R1
R3R4
R5
54
OR1
N
OHR2 R1
R4R5
6
34 Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin
Metathesis, Dehydration, Oxidation, and Tautomerization Kazuhiro Yoshida,* Takeharu Toyoshima, and Tsuneo Imamoto*
Bull. Chem. Soc. Jpn. 2008, 81, 1512-1517
OH
HO RCM
OH
HO
OH OH
HOoror
DehydrationOxidationTautomerization
33 Synthesis of Substituted Phenols by Using the Ring-Closing Metathesis/Isoaromatization
Approach Kazuhiro Yoshida,* Rintaro Narui, and Tsuneo Imamoto*
Chem. Eur. J. 2008, 14, 9706-9713
OR1
R3
R4R5
R2O
R1
R3R4
R5R2
2 3
OHR1
R3R4
R5R2
4
RCM isoaromatization
32
Synthesis of Styrenes Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis Kazuhiro Yoshida,* Yuka Shishikura, Hidetoshi Takahashi, and Tsuneo Imamoto*
Org. Lett. 2008, 10, 2777-2780
31
Marked Deuterium Isotopic Effects on the Enantioselectivity in Rhodium-Catalyzed Asymmetric Hydrogenation of Enamides
Tsuneo Imamoto,* Takuma Itoh, Kazuhiro Yoshida, and Ilya D. Gridnev* Chem. Asian J. 2008, 3, 1636-1641
30
Synthesis of Substituted Benzenes and Phenols via Ring-Closing Olefin Metathesis Kazuhiro Yoshida,* Hidetoshi Takahashi, and Tsuneo Imamoto*
Chem. Eur. J. 2008, 14, 8246-8261
32 Synthesis of Styrenes Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
Kazuhiro Yoshida,* Yuka Shishikura, Hidetoshi Takahashi, and Tsuneo Imamoto* Org. Lett. 2008, 10, 2777-2780
OAcR2
R3
R1R4
R5R6
R2R3
R4
R5R6
R1
612
RCEM
AcOH
R3
R4
R5R6
R1
5
R2OAc
31 Marked Deuterium Isotopic Effects on the Enantioselectivity in Rhodium-Catalyzed
Asymmetric Hydrogenation of Enamides Tsuneo Imamoto,* Takuma Itoh, Kazuhiro Yoshida, and Ilya D. Gridnev*
Chem. Asian J. 2008, 3, 1636-1641
Rh–(S,S)-t-Bu-BisP*
OMe
NHAc
+ H2MeOH, 25 °C
OMe
NHAc
CH3
57% ee
Rh–(S,S)-t-Bu-BisP*
OMe
NHAc
+ D2MeOH, 25 °C
OMe
CH2D
5% ee
NHAcD
30 Synthesis of Substituted Benzenes and Phenols via Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Hidetoshi Takahashi, and Tsuneo Imamoto* Chem. Eur. J. 2008, 14, 8246-8261
CHO
X
M'M ++
OH
or
32 Synthesis of Styrenes Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
Kazuhiro Yoshida,* Yuka Shishikura, Hidetoshi Takahashi, and Tsuneo Imamoto* Org. Lett. 2008, 10, 2777-2780
OAcR2
R3
R1R4
R5R6
R2R3
R4
R5R6
R1
612
RCEM
AcOH
R3
R4
R5R6
R1
5
R2OAc
31 Marked Deuterium Isotopic Effects on the Enantioselectivity in Rhodium-Catalyzed
Asymmetric Hydrogenation of Enamides Tsuneo Imamoto,* Takuma Itoh, Kazuhiro Yoshida, and Ilya D. Gridnev*
Chem. Asian J. 2008, 3, 1636-1641
Rh–(S,S)-t-Bu-BisP*
OMe
NHAc
+ H2MeOH, 25 °C
OMe
NHAc
CH3
57% ee
Rh–(S,S)-t-Bu-BisP*
OMe
NHAc
+ D2MeOH, 25 °C
OMe
CH2D
5% ee
NHAcD
30 Synthesis of Substituted Benzenes and Phenols via Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Hidetoshi Takahashi, and Tsuneo Imamoto* Chem. Eur. J. 2008, 14, 8246-8261
CHO
X
M'M ++
OH
or
32 Synthesis of Styrenes Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
Kazuhiro Yoshida,* Yuka Shishikura, Hidetoshi Takahashi, and Tsuneo Imamoto* Org. Lett. 2008, 10, 2777-2780
OAcR2
R3
R1R4
R5R6
R2R3
R4
R5R6
R1
612
RCEM
AcOH
R3
R4
R5R6
R1
5
R2OAc
31 Marked Deuterium Isotopic Effects on the Enantioselectivity in Rhodium-Catalyzed
Asymmetric Hydrogenation of Enamides Tsuneo Imamoto,* Takuma Itoh, Kazuhiro Yoshida, and Ilya D. Gridnev*
Chem. Asian J. 2008, 3, 1636-1641
Rh–(S,S)-t-Bu-BisP*
OMe
NHAc
+ H2MeOH, 25 °C
OMe
NHAc
CH3
57% ee
Rh–(S,S)-t-Bu-BisP*
OMe
NHAc
+ D2MeOH, 25 °C
OMe
CH2D
5% ee
NHAcD
30 Synthesis of Substituted Benzenes and Phenols via Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Hidetoshi Takahashi, and Tsuneo Imamoto* Chem. Eur. J. 2008, 14, 8246-8261
CHO
X
M'M ++
OH
or
29
Synthesis and Enantioselectivity of P-Chiral Phosphine Ligands Possessing Alkynyl Groups
Tsuneo Imamoto,* Youichi Saitoh, Aya Koide, Tomokazu Ogura, and Kazuhiro Yoshida Angw.Chem. Int. Ed. 2007, 46, 8636-8639
28
t-Bu-QuinoxP* Ligand: Applications in Asymmetric Pd-Catalyzed Allylic Substitution and Ru-Catalyzed Hydrogenation
Tsuneo Imamoto,* Miwako Nishimura, Aya Koide, and Kazuhiro Yoshida J. Org. Chem. 2007, 72, 7413-7416
27
Efficient Synthetic Routes to Aromatic Compounds Using Ring-Closing Olefin Metathesis Followed by Dehydration, Oxidation, and Tautomerization
Kazuhiro Yoshida,* Takeharu Toyoshima, and Tsuneo Imamoto*
Chem. Commun. 2007, 3774-3776
29 Synthesis and Enantioselectivity of P-Chiral Phosphine Ligands Possessing Alkynyl
Groups Tsuneo Imamoto,* Youichi Saitoh, Aya Koide, Tomokazu Ogura, and Kazuhiro Yoshida
Angw.Chem. Int. Ed. 2007, 46, 8636-8639
P H
BH3
MePP
R
R
R = Ph, tBu, iPr3Si, H, Me
LLSS
*
28 t-Bu-QuinoxP* Ligand: Applications in Asymmetric Pd-Catalyzed Allylic Substitution
and Ru-Catalyzed Hydrogenation Tsuneo Imamoto,* Miwako Nishimura, Aya Koide, and Kazuhiro Yoshida
J. Org. Chem. 2007, 72, 7413-7416
N
N
P
PMet-Bu
Me Bu-t
� Pd-catalyzed allylic substitution:up to 98.7% ee
� Ru-catalyzed hydrogenation:up to 99.9% ee
27 Efficient Synthetic Routes to Aromatic Compounds Using Ring-Closing Olefin Metathesis
Followed by Dehydration, Oxidation, and Tautomerization Kazuhiro Yoshida,* Takeharu Toyoshima, and
Tsuneo Imamoto* Chem. Commun. 2007, 3774-3776
M
OHO
aldol product
OH
HO
OH
oror
RCMDehydrationOxidationTautomerization
29 Synthesis and Enantioselectivity of P-Chiral Phosphine Ligands Possessing Alkynyl
Groups Tsuneo Imamoto,* Youichi Saitoh, Aya Koide, Tomokazu Ogura, and Kazuhiro Yoshida
Angw.Chem. Int. Ed. 2007, 46, 8636-8639
P H
BH3
MePP
R
R
R = Ph, tBu, iPr3Si, H, Me
LLSS
*
28 t-Bu-QuinoxP* Ligand: Applications in Asymmetric Pd-Catalyzed Allylic Substitution
and Ru-Catalyzed Hydrogenation Tsuneo Imamoto,* Miwako Nishimura, Aya Koide, and Kazuhiro Yoshida
J. Org. Chem. 2007, 72, 7413-7416
N
N
P
PMet-Bu
Me Bu-t
� Pd-catalyzed allylic substitution:up to 98.7% ee
� Ru-catalyzed hydrogenation:up to 99.9% ee
27 Efficient Synthetic Routes to Aromatic Compounds Using Ring-Closing Olefin Metathesis
Followed by Dehydration, Oxidation, and Tautomerization Kazuhiro Yoshida,* Takeharu Toyoshima, and
Tsuneo Imamoto* Chem. Commun. 2007, 3774-3776
M
OHO
aldol product
OH
HO
OH
oror
RCMDehydrationOxidationTautomerization
29 Synthesis and Enantioselectivity of P-Chiral Phosphine Ligands Possessing Alkynyl
Groups Tsuneo Imamoto,* Youichi Saitoh, Aya Koide, Tomokazu Ogura, and Kazuhiro Yoshida
Angw.Chem. Int. Ed. 2007, 46, 8636-8639
P H
BH3
MePP
R
R
R = Ph, tBu, iPr3Si, H, Me
LLSS
*
28 t-Bu-QuinoxP* Ligand: Applications in Asymmetric Pd-Catalyzed Allylic Substitution
and Ru-Catalyzed Hydrogenation Tsuneo Imamoto,* Miwako Nishimura, Aya Koide, and Kazuhiro Yoshida
J. Org. Chem. 2007, 72, 7413-7416
N
N
P
PMet-Bu
Me Bu-t
� Pd-catalyzed allylic substitution:up to 98.7% ee
� Ru-catalyzed hydrogenation:up to 99.9% ee
27 Efficient Synthetic Routes to Aromatic Compounds Using Ring-Closing Olefin Metathesis
Followed by Dehydration, Oxidation, and Tautomerization Kazuhiro Yoshida,* Takeharu Toyoshima, and
Tsuneo Imamoto* Chem. Commun. 2007, 3774-3776
M
OHO
aldol product
OH
HO
OH
oror
RCMDehydrationOxidationTautomerization
26
An Efficient Route to Benzene and Phenol Derivatives via Ring-Closing Olefin Metathesis Kazuhiro Yoshida,* Shingo Horiuchi, Noriyuki Iwadate, Fumihiro Kawagoe, and
Tsuneo Imamoto* Synlett 2007, 1561-1564
25
Air-stable P-Chiral Bidentate Phosphine Ligand with (1-Adamantyl)methylphosphino Group
Tsuneo Imamoto,* Atsushi Kumada, and Kazuhiro Yoshida Chem. Lett. 2007, 36, 500-501
24
Ring-Closing Olefin Metathesis for the Synthesis of Benzene Derivatives Kazuhiro Yoshida,* Fumihiro Kawagoe, Noriyuki Iwadate, Hidetoshi Takahashi, and
Tsuneo Imamoto* Chem. Asian J. 2006, 1, 611-613
26 An Efficient Route to Benzene and Phenol Derivatives via Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Shingo Horiuchi, Noriyuki Iwadate, Fumihiro Kawagoe, and Tsuneo Imamoto*
Synlett 2007, 1561-1564
OH
[O]
OHCHO
M
RCM
OH
[O]
RCM
O
OH
25 Air-stable P-Chiral Bidentate Phosphine Ligand with (1-Adamantyl)methylphosphino
Group Tsuneo Imamoto,* Atsushi Kumada, and Kazuhiro Yoshida
Chem. Lett. 2007, 36, 500-501
24 Ring-Closing Olefin Metathesis for the Synthesis of Benzene Derivatives
Kazuhiro Yoshida,* Fumihiro Kawagoe, Noriyuki Iwadate, Hidetoshi Takahashi, and Tsuneo Imamoto*
Chem. Asian J. 2006, 1, 611-613
R1R3
R4
R5R6
R2 OH
RCM
C2H4
R3
R4
R5R6
R1R2 OH
H+
H2O
R2
R3
R4
R5R6
R1
up to >99% yield (two steps)
26 An Efficient Route to Benzene and Phenol Derivatives via Ring-Closing Olefin Metathesis
Kazuhiro Yoshida,* Shingo Horiuchi, Noriyuki Iwadate, Fumihiro Kawagoe, and Tsuneo Imamoto*
Synlett 2007, 1561-1564
OH
[O]
OHCHO
M
RCM
OH
[O]
RCM
O
OH
25 Air-stable P-Chiral Bidentate Phosphine Ligand with (1-Adamantyl)methylphosphino
Group Tsuneo Imamoto,* Atsushi Kumada, and Kazuhiro Yoshida
Chem. Lett. 2007, 36, 500-501
24 Ring-Closing Olefin Metathesis for the Synthesis of Benzene Derivatives
Kazuhiro Yoshida,* Fumihiro Kawagoe, Noriyuki Iwadate, Hidetoshi Takahashi, and Tsuneo Imamoto*
Chem. Asian J. 2006, 1, 611-613
R1R3
R4
R5R6
R2 OH
RCM
C2H4
R3
R4
R5R6
R1R2 OH
H+
H2O
R2
R3
R4
R5R6
R1
up to >99% yield (two steps)
23
Enantioselective Hydrogenation of Acyclic Aromatic N-Aryl Imines Catalyzed by an Iridium Complex of (S,S)-1,2-Bis(tert-butylmethylphosphino)ethane
Tsuneo Imamoto,* Noriyuki Iwadate, and Kazuhiro Yoshida Org. Lett. 2006, 8, 2289-2292
22
Synthesis of 2,5-Bis(binaphthyl)phospholes and Phosphametallocene Derivatives and Their Application in Pd-Catalyzed Asymmetric Hydrosilylation
Masamichi Ogasawara,* Azumi Ito, Kazuhiro Yoshida, and Tamio Hayashi* Organometallics 2006, 25, 2715-2718
21
Highly Enantioselective Hydrosilylation of Simple Ketones Catalyzed by Rhodium Complexes of P-Chiral Diphosphine Ligands Bearing tert-Butylmethylphosphino Groups
Tsuneo Imamoto,* Takuma Itoh, Yoshinori Yamanoi, Rintaro Narui, and Kazuhiro Yoshida Tetrahedron: Asymmetry 2006, 17, 560-565
23 Enantioselective Hydrogenation of Acyclic Aromatic N-Aryl Imines Catalyzed by an
Iridium Complex of (S,S)-1,2-Bis(tert-butylmethylphosphino)ethane Tsuneo Imamoto,* Noriyuki Iwadate, and Kazuhiro Yoshida
Org. Lett. 2006, 8, 2289-2292
MeAr1
Ar2N
PPIr+ Me
Me
BARF–
MeAr1
Ar2HN
H2 (1 atm), CH2Cl2, rt
0.5 mol %
up to 99% ee
*
22 Synthesis of 2,5-Bis(binaphthyl)phospholes and Phosphametallocene Derivatives and
Their Application in Pd-Catalyzed Asymmetric Hydrosilylation Masamichi Ogasawara,* Azumi Ito, Kazuhiro Yoshida, and Tamio Hayashi*
Organometallics 2006, 25, 2715-2718
21 Highly Enantioselective Hydrosilylation of Simple Ketones Catalyzed by Rhodium
Complexes of P-Chiral Diphosphine Ligands Bearing tert-Butylmethylphosphino Groups Tsuneo Imamoto,* Takuma Itoh, Yoshinori Yamanoi, Rintaro Narui, and Kazuhiro Yoshida
Tetrahedron: Asymmetry 2006, 17, 560-565
23 Enantioselective Hydrogenation of Acyclic Aromatic N-Aryl Imines Catalyzed by an
Iridium Complex of (S,S)-1,2-Bis(tert-butylmethylphosphino)ethane Tsuneo Imamoto,* Noriyuki Iwadate, and Kazuhiro Yoshida
Org. Lett. 2006, 8, 2289-2292
MeAr1
Ar2N
PPIr+ Me
Me
BARF–
MeAr1
Ar2HN
H2 (1 atm), CH2Cl2, rt
0.5 mol %
up to 99% ee
*
22 Synthesis of 2,5-Bis(binaphthyl)phospholes and Phosphametallocene Derivatives and
Their Application in Pd-Catalyzed Asymmetric Hydrosilylation Masamichi Ogasawara,* Azumi Ito, Kazuhiro Yoshida, and Tamio Hayashi*
Organometallics 2006, 25, 2715-2718
21 Highly Enantioselective Hydrosilylation of Simple Ketones Catalyzed by Rhodium
Complexes of P-Chiral Diphosphine Ligands Bearing tert-Butylmethylphosphino Groups Tsuneo Imamoto,* Takuma Itoh, Yoshinori Yamanoi, Rintaro Narui, and Kazuhiro Yoshida
Tetrahedron: Asymmetry 2006, 17, 560-565
20
An Air-Stable P-Chiral Phosphine Ligand for Highly Enantioselective Transition-Metal-Catalyzed Reactions
Tsuneo Imamoto,* Keitaro Sugita, and Kazuhiro Yoshida J. Am. Chem. Soc. 2005, 127, 11934-11935
19
A New Synthetic Approach to Phenol Derivatives: Use of Ring-Closing Olefin Metathesis Kazuhiro Yoshida* and Tsuneo Imamoto* J. Am. Chem. Soc. 2005, 127, 10470-10471
18
N-H Insertion Reactions of Boc-Amino Acid Amides: Solution- and Solid-Phase Synthesis of Pyrazinones and Pyrazines
Hana Matsushita, Sang-Hyeup Lee, Kazuhiro Yoshida, Bruce Clapham,* Guido Koch, Jürg Zimmermann, and Kim D. Janda*
Org. Lett. 2004, 6, 4627-4629
20 An Air-Stable P-Chiral Phosphine Ligand for Highly Enantioselective
Transition-Metal-Catalyzed Reactions Tsuneo Imamoto,* Keitaro Sugita, and Kazuhiro Yoshida
J. Am. Chem. Soc. 2005, 127, 11934-11935
19 A New Synthetic Approach to Phenol Derivatives: Use of Ring-Closing Olefin Metathesis
Kazuhiro Yoshida* and Tsuneo Imamoto* J. Am. Chem. Soc. 2005, 127, 10470-10471
18 N-H Insertion Reactions of Boc-Amino Acid Amides: Solution- and Solid-Phase Synthesis
of Pyrazinones and Pyrazines Hana Matsushita, Sang-Hyeup Lee, Kazuhiro Yoshida, Bruce Clapham,* Guido Koch, Jürg
Zimmermann, and Kim D. Janda* Org. Lett. 2004, 6, 4627-4629
17
N-H Insertion Reactions of Primary Ureas: The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls
Sang-Hyeup Lee, Kazuhiro Yoshida, Hana Matsushita, Bruce Clapham,* Guido Koch, Jürg Zimmermann, and Kim D. Janda*
J. Org. Chem. 2004, 69, 8829-8835
16
Mechanistic Studies on the Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryltitanate Reagents to a,b-Unsaturated Ketones
Norihito Tokunaga, Kazuhiro Yoshida, and Tamio Hayashi* Proc. Natl. Acad. Sci. USA 2004, 101, 5445-5449
15
High-Throughput Screening by Using a Blue-Fluorescent Antibody Sensor: Evaluation of Cinchona Alkaloids in the Phase-Transfer Catalysis of Asymmetric Alkylation
Masayuki Matsushita,* Kazuhiro Yoshida, Noboru Yamamoto, Peter Wirsching, Richard A. Lerner, and Kim D. Janda*
Angew. Chem. Int. Ed. 2003, 42, 5984-5987
14
A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts: Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-Addition
Tamio Hayashi,* Kazuhito Ueyama, Norihito Tokunaga, and Kazuhiro Yoshida J. Am. Chem. Soc. 2003, 125, 11508-11509
13
A New cine-Substitution of Alkenyl Sulfones with Aryltitanium Reagents Catalyzed by Rhodium: Mechanistic Studies and Catalytic Asymmetric Synthesis of Allylarenes
Kazuhiro Yoshida and Tamio Hayashi* J. Am. Chem. Soc. 2003, 125, 2872-2873
12
Induction of Atropisomeric Chirality on Heavily Substituted Phosphametallocenes Masamichi Ogasawara,* Kazuhiro Yoshida, and Tamio Hayashi*
Organometallics 2003, 22, 1783-1786
11
Generation of Chiral Boron Enolates by Rhodium-Catalyzed Asymmetric 1,4-Addition of 9-Aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) to a,b-Unsaturated Ketones
Kazuhiro Yoshida, Masamichi Ogasawara, and Tamio Hayashi* J. Org. Chem. 2003, 68, 1901-1905
10
Rhodium-Catalyzed Asymmetric 1,4-Addition of 3-Thiopheneboronic Acid to a,b-Unsaturated Carbonyl Compounds Kazuhiro Yoshida and Tamio Hayashi*
Heterocycles 2003, 59, 605-611
9
Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryltitanium Reagents Generating Chiral Titanium Enolates: Isolation as Silyl Enol Ethers
Tamio Hayashi,* Norihito Tokunaga, Kazuhiro Yoshida, and Jin Wook Han J. Am. Chem. Soc. 2002, 124, 12102-12103
8
A New Type of Catalytic Tandem 1,4-Addition-Aldol Reaction Which Proceeds through an (Oxa-p-allyl)rhodium Intermediate
Kazuhiro Yoshida, Masamichi Ogasawara, and Tamio Hayashi* J. Am. Chem. Soc. 2002, 124, 10984-10985
10 Rhodium-Catalyzed Asymmetric 1,4-Addition of 3-Thiopheneboronic Acid to
α ,β-Unsaturated Carbonyl Compounds Kazuhiro Yoshida and Tamio Hayashi*
Heterocycles 2003, 59, 605-611
9 Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryltitanium Reagents Generating
Chiral Titanium Enolates: Isolation as Silyl Enol Ethers Tamio Hayashi,* Norihito Tokunaga, Kazuhiro Yoshida, and Jin Wook Han
J. Am. Chem. Soc. 2002, 124, 12102-12103
8 A New Type of Catalytic Tandem 1,4-Addition-Aldol Reaction Which Proceeds through
an (Oxa-π-allyl)rhodium Intermediate Kazuhiro Yoshida, Masamichi Ogasawara, and Tamio Hayashi*
J. Am. Chem. Soc. 2002, 124, 10984-10985
O O
S
SB(OH)2
94-99% ee
[Rh(OH)((S )-binap)]2(3 mol % Rh)
dioxane/H2O (10/1)40 °C, 24 h
7
Effect of Adjacent Chiral Tertiary and Quaternary Centers on the Metal-Catalyzed Allylic Substitution Reaction
Holly L. Sebahar, Kazuhiro Yoshida, and Louis S. Hegedus* J. Org. Chem. 2002, 67, 3788-3795
6
Synthesis and Characterization of 1,1'-Diphospharuthenocenes Masamichi Ogasawara,* Takashi Nagano, Kazuhiro Yoshida, and Tamio Hayashi*
Organometallics 2002, 21, 3062-3065
5
A Novel Chiral Phosphino-Phosphaferrocene: Its Coordination Behavior and Application to Palladium-Catalyzed Asymmetric Allylic Alkylation
Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi* Organometallics 2001, 20, 3913-3917
4
Synthesis and Characterization of a Novel Chiral Phosphole and Its Derivatives Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi*
Organometallics 2001, 20, 1014-1019
3
2,2'-Bis(diphenylphosphino)-1,1'-biphenyl: New Entry of Bidentate Triarylphosphine Ligand to Transition Metal Catalysts
Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi* Organometallics 2000, 19, 1567-1571
2
Novel Palladium Chiral Phosphino-Oxazoline Complexes: Crystal Structure Studies and Application to Asymmetric Heck Reaction
Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi* Heterocycles 2000, 52, 195-201
1
Synthesis and Application of Novel Chiral Phosphino-Oxazoline Ligands with 1,1’-Binaphthyl Skeleton
Masamichi Ogasawara, Kazuhiro Yoshida, Hiroaki Kamei, Kazuhiko Kato, Yasuhiro Uozumi, and Tamio Hayashi*
Tetrahedron: Asymmetry 1998, 9, 1779-1787
2 Novel Palladium Chiral Phosphino-Oxazoline Complexes: Crystal Structure Studies and
Application to Asymmetric Heck Reaction Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi*
Heterocycles 2000, 52, 195-201
1 Synthesis and Application of Novel Chiral Phosphino-Oxazoline Ligands with
1,1’-Binaphthyl Skeleton Masamichi Ogasawara, Kazuhiro Yoshida, Hiroaki Kamei, Kazuhiko Kato, Yasuhiro Uozumi,
and Tamio Hayashi* Tetrahedron: Asymmetry 1998, 9, 1779-1787
O
TfO
Ph2PN
O
Ph2PN
O
OPh*+ Pd / 1a or 1b
i-Pr2NEt / THFup to 88% ee
(S,S )-1a (S,R )-1b
PhPh
OAc NaCH(COOMe)2
THF
Ph2P N
O
Ph2PN
O
COOMe
PhPh
MeOCO
1a or 1b (2.5 mol %)[PdCl(π-C3H5)]2 (2 mol % Pd) *
up to 91% ee
(S,S )-1a (S,R )-1b
2 Novel Palladium Chiral Phosphino-Oxazoline Complexes: Crystal Structure Studies and
Application to Asymmetric Heck Reaction Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi*
Heterocycles 2000, 52, 195-201
1 Synthesis and Application of Novel Chiral Phosphino-Oxazoline Ligands with
1,1’-Binaphthyl Skeleton Masamichi Ogasawara, Kazuhiro Yoshida, Hiroaki Kamei, Kazuhiko Kato, Yasuhiro Uozumi,
and Tamio Hayashi* Tetrahedron: Asymmetry 1998, 9, 1779-1787
O
TfO
Ph2PN
O
Ph2PN
O
OPh*+ Pd / 1a or 1b
i-Pr2NEt / THFup to 88% ee
(S,S )-1a (S,R )-1b
PhPh
OAc NaCH(COOMe)2
THF
Ph2P N
O
Ph2PN
O
COOMe
PhPh
MeOCO
1a or 1b (2.5 mol %)[PdCl(π-C3H5)]2 (2 mol % Pd) *
up to 91% ee
(S,S )-1a (S,R )-1b
REVIEWS and ACCOUNTS 6
N-Heterocyclic Carbene Ligands Having Planar Chiral Ferrocene Structure Kazuhiro Yoshida* and Risa Yasue
J. Synth. Org. Chem. 2020, 78, 28-40
5
Metathesis Reactions Kazuhiro Yoshida*
Transition-Metal-Mediated Aromatic Ring Construction (2013), 721-742
4
Synthesis of Substituted Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis
Kazuhiro Yoshida,* Tsuneo Imamoto,* and Akira Yanagisawa* J. Synth. Org. Chem. 2009, 67, 876-888
Planar-chiral Ferrocene-based
NHC+ =
3
Rhodium-Catalyzed Additions of Boronic Acids to Carbonyls and Alkenes Kazuhiro Yoshida and Tamio Hayashi
Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine (2005), 171-203
2
Rhodium(I)-Catalyzed Asymmetric Addition of Organometallic Reagents to Electron-Deficient Olefins
Kazuhiro Yoshida and Tamio Hayashi Modern Rhodium-Catalyzed Organic Reactions (2005), 55-77
1
1,4-Addition of Aryl and Alkenyl Metal Reagents Using Rhodium Catalyst Kazuhiro Yoshida and Tamio Hayashi
Gendai Kagaku Zokan (2005), 43 (Saishin Yuki Gosei Kagaku, 2005), 136-147