Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides

Derek Boyd, Narain Sharma, S.A. Haughey, M.A. Kennedy, J.F. Malone, S.D. Shepherd, Christopher Allen, H. Dalton

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. (C) 2003 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)549-559
Number of pages11
JournalTetrahedron
Volume60
Issue number3
DOIs
Publication statusPublished - 12 Jan 2004

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Fingerprint Dive into the research topics of 'Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides'. Together they form a unique fingerprint.

Cite this