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Synfacts 2010(6): 0671-0671  
DOI: 10.1055/s-0029-1219863
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium(I)-Catalyzed Intramolecular [3+2] Cycloaddition of α-Ene-Vinylcyclopropanes

Contributor(s): Mark Lautens, Chit Tsui
Q. Li, G.-J. Jiang, L. Jiao, Z.-X. Yu*
Peking University, Beijing, P. R. of China
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

A novel rhodium-catalyzed intra­molecular [3+2] cycloaddition of α-ene-vinyl­cyclopropane (VCP) 1 was developed. The VCP moiety of the α-ene-VCP acts as a three-carbon synthon instead of the anticipated five-carbon synthon to provide both bicyclo[4.3.0]nonane and bicyclo[5.3.0]decane skeletons 2 in good yield and excellent diastereoselectivity.