Catalytic Enantioselective Hydrostannation of Cyclopropenes

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., 2004, 126 (12), pp 3688–3689
DOI: 10.1021/ja0496928
Publication Date (Web): March 6, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, vlad@uic.edu

Abstract

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The first examples of catalytic enantioselective hydrostannation of the CC double bond of cyclopropenes has been demonstrated. This method allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and enantioselectivity. The facial selectivity of this reaction is entirely controlled by steric factors. A variety of functional groups at C-3 of the cyclopropenes were tolerated.

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History

  • Published In Issue March 31, 2004
  • Received January 16, 2004

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