Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

Marina Rubina, Michael Rubin, and Vladimir Gevorgyan*
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061
J. Am. Chem. Soc., 2002, 124 (39), pp 11566–11567
DOI: 10.1021/ja027095k
Publication Date (Web): September 10, 2002
Copyright © 2002 American Chemical Society
*

 To whom correspondence should be addressed. E-mail:  vlad@uic.edu.

Abstract

Abstract Image

The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

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History

  • Published In Issue October 02, 2002
  • Received May 29, 2002

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