By the same authors

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From the same journal

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

Research output: Contribution to journalArticle

Author(s)

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

Department/unit(s)

Publication details

JournalAngewandte Chemie International Edition
DateAccepted/In press - 18 Feb 2018
DateE-pub ahead of print - 5 Mar 2018
DatePublished (current) - 26 Mar 2018
Issue number14
Volume57
Pages (from-to)3692-3696
Early online date5/03/18
Original languageEnglish

Abstract

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).

Bibliographical note

© 2018 The Authors.

    Research areas

  • Journal Article

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