Tetrahedron Asymmetry p. 1285 - 1294 (1996)
Update date:2022-08-04
Topics:
Svatos, Ales
Hunkova, Zdenka
Kren, Vladimir
Hoskovec, Michal
Saman, David
Valterova, Irena
Vrkoc, Jan
Koutek, Bohumir
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.
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