Baker's yeast-induced asymmetric reduction of alpha-ketosulfides: synthesis of optically active 1-(benzothiazol-2-ylsulfanyl)-2-alkanols, 2-alkanols,and thiiranes

1-(Benzothiazol-2-ylsulfanyl)-2-alkanols 3 were prepared in very high enant iomeric excess by baker's yeast-induced asymmetric reduction of 1-(benzothi azol-2-ylsulfanyl)-2-alkanones 1. Conversion of 3 into optically active sim ple 2-alkanols 4 and thiiranes 2 by reductive desulfurization and base trea tment, respectively, is also described. The absolute configuration of the n ew compounds synthesized has been established by chemical correlation and s pecific rotation comparison. (C) 1999 Elsevier Science Ltd. All rights rese rved.