Asymmetric reactions of α-ketoacid-derived hemiacetals:: Stereoselective synthesis of α-hydroxy acids

被引：15

作者：

Pansare, SV ^{[1
]}

Ravi, RG ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Synth, Poona 411008, Maharashtra, India

来源：

TETRAHEDRON | 1998年 / 54卷 / 48期

关键词：

asymmetric reactions; reduction; Grignard reactions; hydroxy acids;

D O I：

10.1016/S0040-4020(98)00914-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acylation of prolinol with alpha-ketoacid chlorides results in concomitant hemiacetalization of the alpha-keto amide by the prolinol hydroxyl group, (R) or (S) alpha-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) alpha-alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14549 / 14564

页数：16

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