- Enzyme-mediated enantioface-differentiating hydrolysis of α-substituted cycloalkanone enol esters
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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 α-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 applicable to various α-substituted cycloalkanone enol esters, and thereby chiral six-, eight-, ten-, and twelve-membered-ring ketones of 70-96% enantiomeric excess (ee) are easily prepared.
- Matsumoto, Kazutsugu,Tsutsumi, Seiji,Ihori, Tamiko,Ohta, Hiromichi
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p. 9614 - 9619
(2007/10/02)
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