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Synfacts 2007(8): 0839-0839  
DOI: 10.1055/s-2007-968732
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Mediated Synthesis of α-Vinylstannanes

Contributor(s): Mark Lautens, Michael Langer
A. Hamze, O. Provot, J.-D. Brion, M. Alami*
UniversitÉ Paris-Sud, ChÂtenay-Malabry, France
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Vinylstannanes are useful intermediates in palladium-mediated couplings. The synthesis of vinylstannanes with a defined regio- and stereochemistry is still challenging since many methods are influenced by steric factors as well as electronic factors which direct the stannane to either the β-carbon (sterics) or the α-carbon (electronics). In this paper, a method is presented which directs the stannane almost exclusively to the α-carbon presumably by a Z-directing effect of the adjacent double bond.