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Synfacts 2010(5): 0557-0557  
DOI: 10.1055/s-0029-1219698
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Vinyl Sulfones by Isomerization of Allyl Sulfinates

Contributor(s): Mark Lautens, Stephen G. Newman
Q.-L. Xu, L.-X Dai, S.-L. You*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Vinyl sulfones are intermediates which can be used in Michael additions, cycloadditions, or other reactions that require an electron-poor alkene. While exploring the reactivity of allyl sulfinates, the authors discovered an iridium-catalyzed rearrangement-isomerization process which affords vinyl sulfones in excellent yields.