Microbiological Transformations 60. Enantioconvergent Baeyer–Villiger Oxidation  via  a Combined Whole Cells and Ionic Exchange Resin‐Catalysed Dynamic Kinetic Resolution Process | Zendy

Gutiérrez MariaConcepción | Zendy; Furstoss Roland | Zendy; Alphand Véronique | Zendy

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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.

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