1,3-Dipolar Cycloaddition of Azomethine Ylides with Vinyl Sulfones

T. Llamas; R. G. Arrayás; J. C. Carretero

doi:10.1055/s-2006-941916

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Synfacts 2006(7): 0705-0705
DOI: 10.1055/s-2006-941916

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

1,3-Dipolar Cycloaddition of Azomethine Ylides with Vinyl Sulfones

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Llamas, R. G. Arrayás, J. C. Carretero*
Universidad Autónoma de Madrid, Spain

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Publication History

Publication Date:
22 June 2006 (online)

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Significance

The authors describe a copper(I)- catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones. Almost complete exo selectivity is obtained. An extensive ligand screening was performed with TaniaPhos providing the highest ee. Phenyl vinyl sulfone was found to be the optimal dipolarophile and a variety of substituted dipoles afforded the 3-sulfonyl cycloadducts.