Asymmetric reduction of aliphatic short-to long-chain. beta.-keto acids by use of fermenting bakers' yeast

…, H Watabu, H Higashi, T Sakai, S Tsuboi…

Index: Utaka, Masanori; Watabu, Hisashi; Higashi, Hiroshi; Sakai, Takashi; Tsuboi, Sadao; Torii, Sigeru Journal of Organic Chemistry, 1990 , vol. 55, p. 3917 - 3921

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Citation Number: 50

Abstract

Eleven 0-keto acids, ranging from 3-oxobutanoic to 3-oxooctanoic acids, were reduced with fermenting bakers' yeast to the corresponding optically active 0-hydroxy acids, which were isolated as the methyl esters. In all cases, the (R)-hydroxy acids were obtained in 298% ee, except for 3-oxobutanoic acid, which afforded the (S)-hydroxy acid in 86% ee. Inhibition of fermentation was observed for 3-oxoundecanoic to 3-oxotetradecanoic acids, leading to ...