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Synfacts 2008(5): 0508-0508  
DOI: 10.1055/s-2008-1072641
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Gold- and Palladium-Cocatalyzed Vinylstannylation of Alkynes

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
Y. Shi, S. M. Peterson, W. W. Haberaecker, III, S. A. Blum*
University of California, Irvine, USA
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

Carbometalation is a powerful method for the synthesis of olefins from alkynes: However, compared to copper, palladium-catalyzed vinylstannylation is rare. The paper describes an expedient route to the synthesis of tri- and tetra-substituted olefins by monovinylstannylation from alkynes with absolute regio­selectivity and high stereoselectivity. A Au(I)/Pd(0) bimetallic catalyst system that combines the characteristics of two metals suppresses double-addition products.