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

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

Source and publish data:

Tetrahedron Asymmetry p. 1285 - 1294 (1996)

Update date:2022-08-04

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Authors:

Svatos, Ales

Hunkova, Zdenka

Kren, Vladimir

Hoskovec, Michal

Saman, David

Valterova, Irena

Vrkoc, Jan

Koutek, Bohumir

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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.

Full text of DOI:10.1016/0957-4166(96)00145-0

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