M. Zarevucka et al., REDUCTION OF 2-SUBSTITUTED CYCLOHEXANONES BY SACCHAROMYCES-CEREVISIAE, Biocatalysis and biotransformation, 13(4), 1996, pp. 233-243
An enzymatic reduction of 2-substituted cyclohexanones mediated by Sac
charomyces cerevisiae was studied with respect to the stereochemical c
ourse and optical purity of the products. Reduction of ketones 1b-1f r
esulted in separable diastereoisomeric mixtures of cis- and trans-ster
eoisomers of 2-substituted cyclohexanols (2b-2f and 3b-3f) having the
(S) absolute configuration at the chiral center bearing the hydroxyl f
unctionality with high enantiomeric purity. Reduction of ketone 1a yie
lded mixture of cis-(1S, 2R)- and trans-(1R,2R)-stereoisomers (2a and
3a) with lower enantiomeric purity. Changes in the nature of the C(2)-
substituent affect the stereochemical course of the biotransformation.
However, they significantly influenced the enantiomeric purity of the
products. The diastereoselectivity of the process was studied as well
; high diastereoselectivity was observed with the substrates 1a, 1e an
d 1f.