Synlett 2002(7): 1055-1060
DOI: 10.1055/s-2002-32582
LETTER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Sulfide Oxidation with H2O2: A Solid Phase and Array Approach for the Optimisation of Chiral Schiff Base-Vanadium Catalysts

Béatrice Pelotiera, Mike S. Anson*a, Ian B. Campbellb, Simon J. F. Macdonaldb, Ghislaine Priemb, Richard F. W. Jacksonc
a GlaxoSmithKline, Medicines Research Centre, Chemical Development, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK
Fax: +44(134)8764414; e-Mail: msa17004@gsk.com;
b GlaxoSmithKline, Medicines Research Centre, Medicinal Chemistry, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK
c Department of Chemistry, Dainton Building, University of Sheffield
e-Mail: Brook Hill, Sheffield, S3 7HF, UK;
Further Information

Publication History

Received 21 May 2002
Publication Date:
07 February 2007 (online)

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Abstract

Two libraries of chiral Schiff base ligands were synthesised and screened in the vanadium-catalysed oxidation of alkyl aryl sulfides with hydrogen peroxide as terminal oxidant. The vanadium-chiral Schiff base complex 10, readily prepared from 3,5-diiodo-salicylaldehyde and (S)-tert-leucinol, was found to be highly enantioselective. Optically active sulfoxides could thus be obtained in good yields with up to 97% ee.