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Synlett 2007(10): 1501-1506  
DOI: 10.1055/s-2007-982555
LETTER
© Georg Thieme Verlag Stuttgart · New York

Chemoselectivity and Enantioselectivity in Copper-Catalysed Oxidation of Aryl Benzyl Sulfides

Pádraig Kelly, Simon E. Lawrence, Anita R. Maguire*
Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
Fax: +353(21)4274097; e-Mail: a.maguire@ucc.ie;
Further Information

Publication History

Received 19 December 2006
Publication Date:
06 June 2007 (online)

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Abstract

Enantioselective copper-catalysed oxidation of aryl ­benzyl sulfides yields enantioenriched sulfoxides (up to 81% ee) in modest yield. This is the highest enantioselectivity reported using a copper catalyst in enantioselective sulfide oxidation. The enhancement of the enantioselectivity of this method through the use of ­additives is discussed.

Key words

asymmetric catalysis - oxidation - copper - sulfoxides - Schiff bases

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