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Synfacts 2007(8): 0844-0844  
DOI: 10.1055/s-2007-968762
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereo- and Regioselective Silylation of Alkenes Using Silacyclobutanes

Contributor(s): Hisashi Yamamoto, Marina Naodovic
K. Hirano, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Common pathways to vinylsilanes (hydrosilylation and silylmetallation of terminal alkenes) are plagued by stereo- and regioselec­tivity difficulties and limited substrate scope. In this case, utilizing increased Lewis acidity of strained silacyclobutanes, vinylsilanes are accessible with high regio- and stereoselectivity. The variety of alkenes used indicates the superiority of the procedure described. In addition, benzene-fused silacyclobutanes are applicable with equivalent efficiency.