Catalytic Enantioselective Hydroboration of Cyclopropenes

Marina Rubina, Michael Rubin, and Vladimir Gevorgyan*
Chemistry Department, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061
J. Am. Chem. Soc., 2003, 125 (24), pp 7198–7199
DOI: 10.1021/ja034210y
Publication Date (Web): May 23, 2003
Copyright © 2003 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

Abstract Image

2,2-Disubstituted cyclopropyl boronates have been synthesized with high degrees of diastereo- and enantioselectivity via the rhodium-catalyzed asymmetric hydroboration of 3,3-disubstituted cyclopropenes. A strong directing effect of ester and alkoxymethyl substituents has been demonstrated. The directing effect was found to be necessary in achieving high degrees of enantiomeric induction. Selected cyclopropylboronic derivatives were successfully employed in the Suzuki cross-coupling reaction to produce the corresponding optically active aryl- and vinylcyclopropanes in good yields.

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History

  • Published In Issue June 18, 2003
  • Received January 16, 2003

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