Enzyme-mediated enantioface-differentiating hydrolysis of. alpha.-substituted cycloalkanone enol esters

K Matsumoto, S Tsutsumi, T Ihori…

Index: Matsumoto, Kazutsugu; Tsutsumi, Seiji; Ihori, Tamiko; Ohta, Hiromichi Journal of the American Chemical Society, 1990 , vol. 112, # 26 p. 9614 - 9619

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Citation Number: 82

Abstract

Abstract: A new type of enzymatic hydrolysis, enantioface-differentiating hydrolysis of enol esters, is disclosed. As a result of screening, Pichia miso IAM 4682, a type of yeast, was selected as the best strain to perform the enantioselective hydrolysis of enol esters to give a- chiral ketones. For example, incubation of 1-acetoxy-2-methylcyclohexene (4a) with P. miso afforded (S)-2-methylcyclohexanone (5) in high optical yield. This enzymatic hydrolysis is ...