Tetrahedron

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

SV Pansare, RG Ravi

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

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Citation Number: 12

Abstract

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.