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Synfacts 2009(4): 0409-0409  
DOI: 10.1055/s-0028-1087895
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Siloxycarbene Facilitated C-H Functionalization

Contributor(s): Mark Lautens, Jane Panteleev
Z. Shen, V. M. Dong*
University of Toronto, Canada
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

While insertion of carbenes into ­activated C-H bonds is a well-documented transformation, diazo precursors required for such a ­reaction can be difficult to handle. The authors describe the application of the Brook rearrangement in order to obtain siloxycarbene intermediates for an intramolecular benzylic C-H activation. Dihydro­benzofurans are synthesized in good yield and moderate diastereoselectivity.

Review: A. G. Brook Acc. Chem. Res. 1974, 7, 77-84.