Microbiological Transformations 60. Enantioconvergent Baeyer–Villiger Oxidation via a Combined Whole Cells and Ionic Exchange Resin-Catalysed Dynamic Kinetic Resolution Process
✍ Scribed by Maria-Concepción Gutiérrez; Roland Furstoss; Véronique Alphand
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 320 KB
- Volume
- 347
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Abstract
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.