Enantioselective dynamic process reduction of α- and β-tetralone and stereoinversion of resulting alcohols in a selected strain culture

在选定的菌株培养物中,对映选择性动态过程还原 α- 和 β-四氢萘酮并立体转化所得醇

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作者:Tomasz Janeczko, Anna Panek, Alina Swizdor, Jadwiga Dmochowska-Gładysz, Edyta Kostrzewa-Susłow

Abstract

α-Tetralone and β-tetralone were subjected to biotransformation by 14 fungal strains. Enantiomeric purity of the products depended on the reaction time. 3-Day transformation of α-tetralone in Absidia cylindrospora culture gave S-(+)-1,2,3,4-tetrahydro-1-naftol of 92 % ee, whereas longer biotransformation time resulted in decrease of ee value. 3-Day transformation of β-tetralone by the same strain gave predominantly S-(-)-1,2,3,4-tetrahydro-2-naftol, whereas after 9 days of the reaction, the R-enantiomer with 85 % ee was isolated. Transformation of β-tetralone by Chaetomium sp. KCh 6651 gave pure (S)-(-)-1,2,3,4-tetrahydro-2-naftol in high yield at the concentration of 1 g/l. In this process, a non-selective carbonyl reduction was observed, followed by a selective oxidation of the R-alcohol.

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