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Microbiological Transformations 60. Enantioconvergent Baeyer–Villiger Oxidation via a Combined Whole Cells and Ionic Exchange Resin‐Catalysed Dynamic Kinetic Resolution Process
Author(s) -
Gutiérrez MariaConcepción,
Furstoss Roland,
Alphand Véronique
Publication year - 2005
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.200505048
Subject(s) - kinetic resolution , chemistry , enantiopure drug , substrate (aquarium) , resolution (logic) , ionic liquid , organic chemistry , enantioselective synthesis , stereochemistry , catalysis , oceanography , artificial intelligence , geology , computer science
A dynamic kinetic resolution process was applied to an enantioconvergent microbial Baeyer–Villiger oxidation of benzyloxycyclopentanone, rac ‐ 1 . This was achieved by combining a whole cell‐based kinetic resolution and an anion exchange resin‐catalysed in situ racemisation. Several resins were screened according to their capacity to catalyse the racemisation of 1 . As compared to our previous results, the presence of weakly basic Lewatit MP62 in biotransformations of 1 allowed a three‐fold improvement of usable substrate concentration and afforded nearly enantiopure lactone ( R )‐ 2 (97% ee) in preparative (isolated) yields higher than 84%. Noyori's model was applied to this reaction and allowed kinetic constants determination.