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Synfacts 2010(1): 0055-0055  
DOI: 10.1055/s-0029-1218502
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Cyclopropanation of Allenes Catalyzed by a Rhodium(II) Complex

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
T. M. Gregg*, M. K. Farrugia, J. R. Frost
Canisius College, Buffalo, USA
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

The authors reported the rhodium-catalyzed enantioselective cyclopropanation of ­allenes with methyl aryldiazoacetate to afford alkylidene cyclopropanes. The cyclopropane products of monosubstituted allene substrates were obtained in good yields, while yields for 1,1-disubstituted allenes were significantly lower. Interestingly, the substitution with silicon on the allene substrate has a strong accelerating effect on the reaction.