Tetrahedron

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

SV Pansare, RG Ravi

文献索引：Pansare, Sunil V.; Ravi, R. Gnana Tetrahedron, 1998 , vol. 54, # 48 p. 14549 - 14564

全文：HTML全文

被引用次数: 12

摘要

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