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Synfacts 2006(4): 0355-0355  
DOI: 10.1055/s-2006-932048
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Three-Component Tandem Reaction to Synthesize Tetrasubstituted Olefins

Contributor(s): Mark Lautens, Josephine Yuen
M. Xie*, J. Wang, X. Gu, Y. Sun, S. Wang*
Anhui Normal University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

A stereoselective one-pot three-component allylzincation of acetylenic sulfones/Negishi cross-coupling of vinyl zinc bromides with halohydrocarbons is described. Tetrasubstituted olefins containing a 1,4-diene structural unit were prepared with complete regio- and stereocontrol. The allylzincation proceeded with syn-addition and the geometry of the double bond is preserved during the Negishi coupling.