Baker's yeast-mediated reduction of cyclohexanones containing a nitro or a sulfonyl group at C-3

Article abstract of DOI:10.1016/S0957-4166(97)00370-4

Baker's yeast-mediated reduction of 3-(nitromethyl)-, 3-(phenylsulfonyl)-, and 3-[(phenylsulfonyl)methyl]-cyclohexanones 1a,c,d led to the delivery of a hydride to the re-face of the prochiral ketones to provide cyclohexanols (1S,3S)- and (1S,3R)-2a,c,d with high enantioselectivities 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.