Download PDF
Synfacts 2010(10): 1149-1149  
DOI: 10.1055/s-0030-1258655
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Silacyclobutanes

Contributor(s): Mark Lautens, David Candito
B. J. Ager, L. E. Bourque, K. M. Buchner, K. A. Woerpel*
University of California, Irvine, USA
Further Information

Publication History

Publication Date:
22 September 2010 (online)

    Permissions and Reprints

Significance

Silacyclobutanes are a unique class of compounds with a variety of chemical applications. Typically, these silanes have been synthesized via Wurtz-type coupling or [2+2] cycloadditions. Building upon previous work in the area of silylene transfer reactions, the authors report on the silver-catalyzed silylene transfer to allylic sulfides, generating silacyclobutanes stereoselectively. The authors go on to demonstrate the carbonyl insertion reactions of these products to generate oxasilacyclohexanes.