BAKERS YEAST-MEDIATED REDUCTION OF CYCLOHEXANONES CONTAINING A NITRO OR A SULFONYL GROUP AT C-3

Baker's yeast-mediated reduction of 3-(nitromethyl)-, 3-(phenylsulfony l)-, and 3-[(phenylsulfonyl)methyl]-cyclohexanone la,c,a led to the de livery of a hydride to the re-face of the prochiral ketones to provide cyclohexanols (1S,3S)- and (1S,3R)-2a,c,d with high enantioselectivit ies in good yields. The remote nitro and sulfonyl groups, in contrast to alkyl and sulfenyl groups, may play an important role in binding to an enzyme. (C) 1997 Elsevier Science Ltd.