Biotransformations of γ-methyl-β-ketosulfones: Stereoselectivity of 3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts

Article abstract of DOI:10.1016/0957-4166(96)00145-0

The stereoselectivity of the reduction of rac-3-methyl-1-(phenylsulfonyl)hexan-2-one (1) to 3-methyl-1-(phenylsulfonyl)hexan-2-ol (2) diastereomers by more than 20 yeasts was studied. Reduction of carbonyl group in 1 proceeds with a high Re-face enantioselectivity: Candida guillermondii (98.9% e.e), C. zeylanoides (>99.9%), and Kloeckera apiculata (99.6%), respectively and the (R)-1 enantiomer usually reacted faster. The enantioselectivity was determined by GC on chiral cyclodextrine phases and absolute configurations of products were assigned by NMR spectroscopy and a chemical correlation.