Asymmetric reduction of carbonyl compounds by yeast. IV. Preparation of optically active β-hydroxy sulfides, sulfoxides and sulfones

Abstract

Reduction of simple β-keto sulfides, β-keto sulfoxides and P-keto sulfones by an actively fermenting mutant of Saccharomyces cerevisiae proceeds readily and affords good yields of the corresponding optically active secondary alcohols. For example, 1-(benzylthio)propan-2-one gave optically pure (S)-(+)-1-(benzylthio)propan-2-ol and 1- (phenylsulfonyl)propan-2-one gave optically pure (S)-(+)-1- (phenylsulfonyl)propan-2-ol. In the reductions of racemic β-keto sulfoxides the enantiomers were reduced at sufficiently different rates to enable isolation of an optically active ketone and of an optically active β-hydroxy sulfoxide. Hence, 1-(phenylsulfinyl)propan-2-one gave (S)-(-)-1-(phenyl-sulfinyl)propan-2-one and (RS,SC)-(+)-1- (phenylsulfinyl)propan-2-ol.