Microbiological Transformations 60. Enantioconvergent Baeyer-Villiger Oxidationvia a Combined Whole Cells and Ionic Exchange Resin-Catalysed Dynamic Kinetic Resolution Process

Autor:	Maria-Concepcion Gutiérrez, Véronique Alphand, Roland Furstoss
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Enantiopure drug Ion exchange Chemistry Scientific method Ionic bonding Organic chemistry General Chemistry Ion-exchange resin Lactone Baeyer–Villiger oxidation Kinetic resolution
Zdroj:	Advanced Synthesis & Catalysis. 347:1051-1059
ISSN:	1615-4169 1615-4150
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ad1b42bfe8b55e5b5b68e28706dda32c https://doi.org/10.1002/adsc.200505048 Zobrazit plný text záznamu Plný text