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

Autor:	Jan Vrkoč, Zdenka Huňková, Bohumír Koutek, Vladimír Křen, Aleš Svatoš, David Šaman, Irena Valterová, Michal Hoskovec
Rok vydání:	1996
Předmět:	Stereochemistry Organic Chemistry Diastereomer Nuclear magnetic resonance spectroscopy Carbonyl group Catalysis Chemical correlation Kloeckera apiculata Inorganic Chemistry chemistry.chemical_compound chemistry Stereoselectivity Physical and Theoretical Chemistry Enantiomer Beta (finance)
Zdroj:	Tetrahedron: Asymmetry. 7:1285-1294
ISSN:	0957-4166
DOI:	10.1016/0957-4166(96)00145-0
Popis:	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 (989% 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fc69594f6bdf96be1daa683df94e1a72 https://doi.org/10.1016/0957-4166(96)00145-0 Zobrazit plný text záznamu Full Text from ScienceDirect