Asymmetric Baeyer–Villiger Biooxidation of α-Substituted Cyanocyclohexanones: Influence of the Substituent Length on Regio- and Enantioselectivity

Autor:	Véronique Alphand, Roland Furstoss, Erika Kozma, Nathalie Berezina
Rok vydání:	2007
Předmět:	Chemistry Stereochemistry Substituent Regioselectivity General Chemistry Monooxygenase medicine.disease_cause Catalysis Kinetic resolution chemistry.chemical_compound Enantiopure drug Biotransformation medicine Escherichia coli
Zdroj:	Advanced Synthesis & Catalysis. 349:2049-2053
ISSN:	1615-4169 1615-4150
Popis:	Cells of Escherichia coli expressing cyclo- hexanone monooxygenase catalyzed a highly enan- tioselective Baeyer-Villiger oxidation of a-substi- tuted cyanocyclohexanones, leading to the corre- sponding enantiopure caprolactones (ees > 97 %). Classical kinetic resolution and regiodivergent par- allel kinetic resolution patterns were observed, de- pending on the length of the linear chain at the alpha position. Regioselectivitywas compared with that of chemical BV oxidations. Cells revealed an outstanding stabilitysince 50 % of the specific BV activitywas retained after 42 day s of storage, which facilitates their use in biotransformations.
Databáze:	OpenAIRE
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