Biotransformations of gamma-methyl-beta-ketosulfones:stereoselectivity of 
3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts

Svatoš, Aleš; Hunkova, Z.; Kren, V.; Hoskovec, M.; Saman, D.; Valterova, I.; Vrkoc, J.; Koutek, B.

doi:10.1016/0957-4166(96)00145-0

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Biotransformations of gamma-methyl-beta-ketosulfones:stereoselectivity of 3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts

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Svatoš, A., Hunkova, Z., Kren, V., Hoskovec, M., Saman, D., Valterova, I., et al. (1996). Biotransformations of gamma-methyl-beta-ketosulfones:stereoselectivity of 3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts. Tetrahedron: Asymmetry, 7(5), 1285-1294. doi:10.1016/0957-4166(96)00145-0.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-0F31-3

Abstract

The stereoselectivity of the reduction of rac-3-methyl1-(phenylsulfonyl)hexan-2-one (1) to 3-methyl1-(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. Copyright (C) 1996 Elsevier Science Ltd