Synlett 2006(10): 1569-1573  
DOI: 10.1055/s-2006-944187
LETTER
© Georg Thieme Verlag Stuttgart · New York

Kinetic Resolution in Vanadium-Catalyzed Sulfur Oxidation as an Efficient Route to Enantiopure Aryl Benzyl Sulfoxides

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;
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Publikationsverlauf

Received 28 December 2005
Publikationsdatum:
12. Juni 2006 (online)

Abstract

Enantiopure aryl benzyl sulfoxides can be prepared ­using vanadium-Schiff base catalyzed sulfide oxidation and kinetic resolution of the resulting sulfoxide. The kinetic resolution can be effected in combination with asymmetric sulfide oxidation or instead starting from the racemic sulfoxide.

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We are very grateful for the assistance and advice received from Carsten Bolm in this area. Ligand 2 was first reported by Anson, see ref. 7f.