Dynamic Baeyer-Villiger

Dynamic kinetic resolution process was also applied to biocatalytic Baeyer-Villiger oxidations. The recombinant E. coli expressing the cyclohexanone monooxygenase from A. calcoaceticus was used for the oxidation of racemic... 

Application of dynamic kinetic resolution has also been reported in a whole-cell enzymatic Baeyer-Villiger process. While this was initially done using slightly basic conditions, Furstoss and Alphand have more recently reported the use of a weakly basic anion exchange resin to promote racemization of the slow oxidizing enantiomer 99 to the fast enantiomer 100.53 Baeyer-Villiger oxidation using recombinant E. coli to overexpress the CHMO from A. calcoaceticus provided excellent yield and % ee of lactone 101. 

Gutierrez M-C, Furstoss R, Alphand V (2005) Microbiological transformations 60. Enantioconvergent Baeyer-Villiger oxidation via a combined whole cells and ionic exchange resin-catalysed dynamic kinetic resolution process. Adv Synth Catal 347(7-8) 1051-1059. doi 10.1002/adsc.200505048... 

N. Berezina, V. Alphand, R. Furstoss, Microbiological transformations. Part 51 The first example of a dynamic kinetic resolution process applied to a microbiological Baeyer-Villiger oxidation. Tetrahedron Asymmetry 13 (2002) 1953-1955. 

A. Rioz-Martinez, A. Cuetos, C. Rodriguez, G. de Gonzalo, 1. Lavandera, M.W. Fraaije, V. Gotor, Dynamic kinetic resolution of alpha-substituted beta-ketoesters catalyzed by Baeyer-Villiger monooxygenases access to enantiopure alpha-hydroxy esters, Angew. Chem.-Int. Ed. 50 (2011) 8387-8390. 

---