Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines

被引:143
作者
Okamoto, Kazuhiro [1 ]
Hayashi, Tamio [1 ]
Rawal, Viresh H. [2 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; N-TOSYLARYLIMINES; DEFICIENT OLEFINS; STEERING LIGANDS; HIGH-PERFORMANCE; ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE SYNTHESIS; PHENYLBORONIC ACID; TITANIUM REAGENTS;
D O I
10.1039/b904624k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rhodium-catalyzed asymmetric arylation of imines using electronically and sterically-modified chiral diene ligands gave the corresponding diarylmethylamines in high yield and with high enantioselectivity using just 0.3 mol% of catalyst.
引用
收藏
页码:4815 / 4817
页数:3
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[1]   TRANS-INFLUENCE - ITS MEASUREMENT AND SIGNIFICANCE [J].
APPLETON, TG ;
CLARK, HC ;
MANZER, LE .
COORDINATION CHEMISTRY REVIEWS, 1973, 10 (3-4) :335-422
[2]   Expanding the C2-symmetric bicyclo[2.2.1]hepta-2,5-diene ligand family:: Concise synthesis and catalytic activity in rhodium-catalyzed asymmetric addition [J].
Berthon-Gelloz, Guillaume ;
Hayashi, Tamio .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8957-8960
[3]   High performance of a chiral diene-rhodium catalyst for the asymmetric 1,4-addition of arylboroxines to α,β-unsaturated ketones [J].
Chen, FX ;
Kina, A ;
Hayashi, T .
ORGANIC LETTERS, 2006, 8 (02) :341-344
[4]   Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].
Darses, S ;
Genet, JP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327
[5]   Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors [J].
Defieber, C ;
Paquin, JF ;
Serna, S ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (21) :3873-3876
[6]   Chiral olefins as steering ligands in asymmetric catalysis [J].
Defieber, Christian ;
Gruetzmacher, Hansjoerg ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502
[7]   Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids [J].
Duan, Hai-Feng ;
Jia, Yi-Xia ;
Wang, Li-Xin ;
Zhou, Qi-Lin .
ORGANIC LETTERS, 2006, 8 (12) :2567-2569
[8]  
Evans J.A., 1971, Chem. Commun, P197
[9]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[10]   Highly practical catalytic asymmetric 1,4-addition of arylboronic acids in water using new hydrophilic chiral bicyclo[3.3.0] diene ligands [J].
Feng, Chen-Guo ;
Wang, Zhi-Qian ;
Shao, Cheng ;
Xu, Ming-Hua ;
Lin, Guo-Qiang .
ORGANIC LETTERS, 2008, 10 (18) :4101-4104