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

Abstract
Phenylthioacetone (1), (±)-phenylsulfmylacetone (5) and phenylsulfonylacetone (3) were reduced by fermenting bakers’ yeast to produce the corresponding alcohols of (S)-configuration. 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.

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