Enantioselective synthesis of β-hydroxy carboxylic acids:: direct conversion of β-oxocarboxylic acids to enantiomerically enriched β-hydroxy carboxylic acids via neighboring group control

被引：29
|
作者：
Wang, Z [1 ]
Zhao, CL [1 ]
Pierce, ME [1 ]
Fortunak, JM [1 ]
机构：
[1] Dupont Merck Pharmaceut Co, Res & Dev, Chambers Works, Deepwater, NJ 08023 USA
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 02期
关键词：
D O I：
10.1016/S0957-4166(98)00502-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
beta-Oxocarboxylic acids can be reduced to the corresponding beta-hydroxy carboxylic acids employing DIP-Cl(TM) as a reducing agent. The beta-carboxylic substituent exerts a remarkable neighboring group effect on the reduction. The reaction presumably proceeds in an intramolecular fashion through a 'rigid' bicyclic transition state assembly, which produces enantioselectivities approaching 99%. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：225 / 228
页数：4
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