Stereochemical Control in Microbial Reduction. 9. Diastereoselective Reduction of 2-Alkyl-3-oxobutanoate with Bakers' Yeast

K Nakamura, T Miyai, A Nagar, S Oka…

Index: Nakamura, Kaoru; Miyai, Takehiko; Nagar, Ashish; Oka, Shinzaburo; Ohno, Atsuyoshi Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 4 p. 1179 - 1187

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Citation Number: 68

Abstract

Bakers' yeast reduces esters of 2-alkyl-3-oxobutanoic acid (CH 3 COCHRCO 2 R′; R= methyl, ethyl, propyl, propargyl, and allyl) into the corresponding (S)-hydroxy esters with exclusive stereoselectivity, while the configuration at the 2-position of the hydroxy esters is either S (anti) or R (syn) depending on the structure of the alkoxyl group in the carboalkoxyl moiety of the ester. Oftenly, the stereoselectivity with respect to the 2-position is not ...