Asymmetric construction of quaternary carbon stereocenters: High stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes

被引：30

作者：

Adhikari, S ^{[1
]}

Caille, S ^{[1
]}

Hanbauer, M ^{[1
]}

Ngo, VX ^{[1
]}

Overman, LE ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol051172+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aidehydes having nitrogen or oxygen substituents at the a carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1)

引用

页码：2795 / 2797

页数：3

共 18 条

[1] METAL VERSUS SILYL TRIFLATE CATALYSIS IN THE MUKAIYAMA ALDOL ADDITION-REACTION
CARREIRA, EM
SINGER, RA
[J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4323 - 4326
[2] CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P997
[3] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
Christoffers, J
Baro, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
[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] Stereoselective formation of quaternary carbon centers and related functions
Denissova, I
Barriault, L
[J]. TETRAHEDRON, 2003, 59 (51) : 10105 - 10146
[9] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters
Douglas, CJ
Overman, LE
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5363 - 5367
[10] Garner P., 1998, Org. Synth., V9, P300

← 1 2 →