Enantioselective synthesis of α-hydroxy carboxylic acids: direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via …

Z Wang, B La, JM Fortunak, XJ Meng, GW Kabalka

Index: Wang, Zhe; La, Brittany; Fortunak, Joseph M.; Meng, Xian-Jun; Kabalka, George W. Tetrahedron Letters, 1998 , vol. 39, # 31 p. 5501 - 5504

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Citation Number: 57

Abstract

α-Oxocarboxylic acids can be reduced to the corresponding α-hydroxy carboxylic acids employing DIP-C1tm as a reducing agent. The α-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%.