Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes

Derek R. Boyd*, Narain D. Sharma, John F. Malone, Vera Ljubez, Deirdre Murphy, Steven D. Shepherd, Christopher C R Allen

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Enantiopure β-hydroxy sulfoxides and catechol sulfoxides were obtained, by chemoenzymatic synthesis, involving dioxygenase-catalysed benzylic hydroxylation or arene cis-dihydroxylation and cis-diol dehydrogenase-catalysed dehydrogenation. Absolute configurations of chiral hydroxy sulfoxides were determined by X-ray crystallography, ECD spectroscopy and stereochemical correlation. The application of a new range of β-hydroxy sulfoxides as chiral ligands was examined.

Original languageEnglish
Pages (from-to)2651-2664
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number9
Early online date01 Feb 2016
DOIs
Publication statusPublished - 07 Mar 2016

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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