Rhodium-catalyzed asymmetric construction of quaternary carbon stereocenters: Ligand-dependent regiocontrol in the 1,4-addition to substituted maleimides

被引:179
作者
Shintani, R [1 ]
Duan, WL [1 ]
Hayashi, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
D O I
10.1021/ja061430d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to substituted maleimides has been described. The regioselectivity in this reaction is controlled by the choice of ligand (dienes or bisphosphines), and 1,4-adducts with a quaternary stereocenter can be obtained with high regio- and enantioselectivity by the use of (R)-H8-binap. Copyright © 2006 American Chemical Society.
引用
收藏
页码:5628 / 5629
页数:2
相关论文
共 45 条
[1]   A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from(-)-8-aminomenthol [J].
Andrés, C ;
Duque-Soladana, JP ;
Pedrosa, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4282-4288
[2]   An easy access to (S)-pyrrolidinones and -pyrrolidines from chiral benzylic malonates [J].
Arzel, P ;
Freida, V ;
Weber, P ;
Fadel, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :3877-3881
[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]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[5]  
2-V
[6]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[7]  
2-V
[8]   Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: Construction of stereogenic quaternary centers [J].
d'Augustin, M ;
Palais, L ;
Alexakis, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1376-1378
[9]   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
[10]   Stereoselective formation of quaternary carbon centers and related functions [J].
Denissova, I ;
Barriault, L .
TETRAHEDRON, 2003, 59 (51) :10105-10146