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Synfacts 2010(3): 0329-0329  
DOI: 10.1055/s-0029-1219330
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereospecific Intramolecular Alkynylcyclopropanation of Olefins

Contributor(s): Mark Lautens, Jane Panteleev
K. Komeyama*, N. Saigo, M. Miyagi, K. Takaki*
Hiroshima University, Higashi-Hiroshima, Japan
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The authors describe a reaction of propargylic alcohols with alkenes to give cyclopropanes under Lewis acid catalysis. Enyne cyclizations are well known under transition-metal cata­lysis (i.e., Rh, Au, Pd; see Review below) and the described activation of the propargylic alcohols with the more accessible Lewis acids is noteworthy.

Review: For a review on enyne cycloisomerizations, see: V. Michelet, P. Y. Toullec, J.-P. Genêt Angew. Chem. Int. Ed. 2008, 47, 4268-4315.