Biocatalytic Conversion of Cyclic Ketones Bearing α-Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium-Sized Carbocycles

Charlotte Morrill, Chantel N Jensen, Xavier Just-Baringo, Gideon Grogan, Nicholas Turner, David John Procter

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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).

Original languageEnglish
Pages (from-to)3692-3696
Number of pages5
JournalAngewandte Chemie International Edition
Issue number14
Early online date5 Mar 2018
Publication statusPublished - 26 Mar 2018

Bibliographical note

© 2018 The Authors.


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