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| - Access to Optically Pure 4- and 5-Substituted Lactones: A Case ofChemical−Biocatalytical Cooperation
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| - Optically pure or highly enantiomerically enriched 4- and 5-substituted lactones are rather difficultto obtain. Chemical or enzymatic syntheses alone are not particularly successful. A combination ofchemical catalysis and biocatalysis, however, provides a convenient route to a variety of these usefulchiral compounds. In this paper we describe the synthesis of several optically pure 4- and5-substituted lactones obtained via whole cell-catalyzed Baeyer−Villiger oxidations of highlyenantiomerically enriched 3-alkyl cyclic ketones. Such chiral ketones are readily accessed by recentlydeveloped copper-catalyzed asymmetric conjugate reductions of the corresponding enones. A veryhigh proximal regioselectivity and complete chirality transfer was obtained by employing biologicalBaeyer−Villiger oxidations, using recombinant E. coli strains that overexpress cyclopentanonemonooxygenase (CPMO). A comparative study showed that CPMO gives superior results to thoseobtained with cyclohexanone monooxygenase (CHMO) catalyzed oxidations.
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