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Asymmetric Baeyer–Villiger Biooxidation of α‐Substituted Cyanocyclohexanones: Influence of the Substituent Length on Regio‐ and Enantioselectivity
Author(s) -
Berezithalie,
Kozma Erika,
Furstoss Roland,
Alphand Véronique
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700150
Subject(s) - enantiopure drug , chemistry , regioselectivity , kinetic resolution , enantioselective synthesis , substituent , baeyer–villiger oxidation , stereochemistry , cyclohexanone , combinatorial chemistry , catalysis , organic chemistry
Cells of Escherichia coli expressing cyclohexanone monooxygenase catalyzed a highly enantioselective Baeyer–Villiger oxidation of α‐substituted cyanocyclohexanones, leading to the corresponding enantiopure caprolactones ( ee s >97 %). Classical kinetic resolution and regiodivergent parallel kinetic resolution patterns were observed, depending on the length of the linear chain at the alpha position. Regioselectivity was compared with that of chemical BV oxidations. Cells revealed an outstanding stability since 50 % of the specific BV activity was retained after 42 days of storage, which facilitates their use in biotransformations.