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Synfacts 2005(3): 0311-0311  
DOI: 10.1055/s-2005-921643
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Sp3 C-H Functionalization via a Lewis Acid-Catalyzed Redox Event

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. J. Pastine, K. M. McQuaid, D. Sames*
Columbia University, New York, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

This paper describes very mild ­conditions (ambient temperature without rigorous exclusion of moisture) for the hydroalkylation of electron-deficient olefins. Lewis acid catalysts [BF3⟨Et2O, Sc(OTf)3 or PtCl4] provided spiro and bicyclic compounds in high yield (many >95%). The process is believed to proceed through a 1,5-hydride shift and compounds lacking the 1,5-relationship (i.e. 1,4- and 1,6-) did not afford any product. High diastereoselectivity could be obtained (up to >15:1) in some cases and the reaction showed a relatively broad scope of substrates.