Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Biocatalytic conversion of cyclic ketones bearing alpha-quaternary stereocenters to lactones in an enantioselective radical approach to medium-sized carbocycles

Charlotte Morrill, Nicholas Turner, David John Procter, Xavier Just-Baringo, Chantel Jensen, Gideon Grogan
Cyclic ketones bearing alpha-quaternary stereocenters undergo efficient kinetic resolution using cyclohexanone monooxygenase (CHMO) from Acinetobacter calcoaceticus. Lactones possessing tetrasubstituted stereocenters are obtained with high enantioselectivity (up to >99% ee) and complete chemoselectivity. Preparative scale biotransformations were exploited in conjunction with a SmI2-mediated cyclization process to access complex, enantiomerically enriched cycloheptan- and cycloctan-1,4-diols. In a parallel approach to structurally distinct products, enantioenriched ketones from the resolution bearing an alpha- all carbon quaternary stereocenter were used in a SmI2-mediated cyclization process to give cyclobutanol products (up to >99% ee).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201800121

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