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Synfacts 2009(12): 1359-1359  
DOI: 10.1055/s-0029-1218253
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Reaction of Silylene with Epoxides and Aldehydes

Contributor(s): Mark Lautens, Jane Panteleev
M. Prévost, K. A. Woerpel*
University of California, Irvine, USA
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

The authors discuss an application of a silylene precursor 2 in the synthesis of structurally unique trans-dioxasilacyclooctenes. The reaction of vinylepoxides with 2 yields a silaoxetane intermediate 3, which thereafter reacts with aldehydes to give the desired products 4. The diastereoselectivity of the reaction is excellent and only a single isomer is generally observed.