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

页码：225 / 228

页数：4

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