Microbiological Transformations 57. Facile and Efficient Resin-Based in Situ SFPR Preparative-Scale Synthesis of an Enantiopure “Unexpected” Lactone Regioisomer via a Baeyer−Villiger Oxidation Process

[reaction: see text] The microbiological Baeyer-Villiger oxidation of (-)-bicyclo[3.2.0]hept-2-en-6-one allowed exclusive formation of the "unexpected" lactone regioisomer in 84% yield, high chemical purity, and enantiopure form. Substrate (25 g) was transformed in a 1 L bubble column reactor, following a in situ substrate feeding/product removal methodology, which afforded high volumetric productivity (1.2 g L(-)(1) h(-)(1)). This illustrates the high "sustainable chemistry" advantages of such a process, simply conducted in aqueous medium, at room temperature and using atmospheric oxygen.