Comparative Asymmetric Reduction of Phenylthioacetone, (±)-Phenylsulfinylacetone and Phenylsulfonylacetone with Fermenting Bakers'Yeast

Abstract

Phenylthioacetone (1), (±)-phenylsulfinylacetone (5) and phenylsulfonylacetone (3) were reduced by fermenting bakers' yeast to produce the corresponding alcohols of (S)-configura-tion. Sulfone 3 was reduced most readily. Reduction of (±)-5 gave a mixture of (S)-5 and (S)_c-(R)_s-2-hydroxypropyl phenyl sulfoxide (6), showing that (R)-5 is reduced more easily than (S)-5. The order of reducibility of four sulfur analogs is shown as 3>(R)-5>1>(S)-5.