ENANTIOSELECTIVE SYNTHESIS OF α-HYDROXYTHIOACETALS BY THE BAKER’S YEAST REDUCTION OF α-KETOTHIOACETALS

Abstract

Asymmetric reduction of a-ketothioacetals was achieved by fermenting baker’s yeast to afford optically pure α-hydroxythioacetals which play as equivalents of valuable α-hydroxy aldehydes. The utility of the present method was demonstrated in the stereo-selective syntheses of (4S,5S)- and (4S,5R)-4,5-dihydroxydecanoic acid γ-lactones from (S)-(−)-1-(1,3-dithian-2-yl)-1,4-butanediol.