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

Research output: Contribution to journalArticle

  • External authors:
  • Charlotte Morrill
  • Chantel Jensen
  • Xavier Just-Baringo
  • Gideon Grogan

Abstract

Cyclic ketones bearing α-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 α- all carbon quaternary stereocenter were used in a SmI2-mediated cyclization process to give cyclobutanol products (up to >99% ee).

Bibliographical metadata

Original languageEnglish
Pages (from-to)3692-3696
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number14
Early online date2 Feb 2018
DOIs
Publication statusPublished - 26 Mar 2018

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