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Development of the enzyme‐catalysed Baeyer–Villiger reaction as a useful technique in organic synthesis
Author(s) -
Roberts Stanley M.,
Willetts Andrew J.
Publication year - 1993
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530050510
Subject(s) - chemistry , formate dehydrogenase , monooxygenase , cofactor , pseudomonas putida , biocatalysis , formate , stereoselectivity , alcohol dehydrogenase , organic synthesis , enzyme , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , reaction mechanism , cytochrome p450
The current practices of using monooxygenase enzymes to perform regio‐ and stereoselective oxidation reactions in organic syntheses are reviewed. The isolation of a monooxygenase from Pseudomonas putida NCIMB 10007 and its use in the conversion of bicyclo[3.2.0]hept‐2‐en‐6‐one into two isomeric optically active lactones is described. The monooxygenase utilises NADH as cofactor and NADH‐recycling is accomplished using formate and formate dehydrogenase. As alternative methodology, it is shown that a secondary alcohol can be converted into a chiral lactone using a dehydrogenase and a monooxygenase working in tandem with in situ cofactor recycling. © 1993 Wiley‐Liss, Inc.