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Synfacts 2006(1): 0033-0033  
DOI: 10.1055/s-2005-921678
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Chiral Sulfoxide Synthesis via Vanadium-Catalyzed Oxidation of Sulfides

Contributor(s): Mark Lautens, Y. Eric Fang
C. Drago, L. Caggiano, R. F. W. Jackson*
University of Sheffield, UK
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

Highly enantioenriched aryl alkyl sulfoxides were synthesized by vanadium(V)-catalyzed asymmetric oxidation of sulfides. This convenient process used low loadings of VO(acac)2/chiral Schiff-base ligand and a slight excess of H2O2 (1.2 equiv), affording good yield and good to excellent ee. It was found that in chloroform at 0 ºC, the R- and S-sulfoxides react at very different rates so that the undesired minor S-enantio­mer was further oxidized to sulfone whereas the R-enantiomer remained untouched. This process gave the desired enantiomer in good yield and >99.5% ee on relatively large scale (60 mmol) after one recrystallization.