A Rhodium-Catalyzed C−H Activation/Cycloisomerization Tandem

Christophe Aïssa and Alois Fürstner*
Max-Planck-Institut fr Kohlenforschung, D-45470 Mlheim/Ruhr, Germany
J. Am. Chem. Soc., 2007, 129 (48), pp 14836–14837
DOI: 10.1021/ja0746316
Publication Date (Web): November 10, 2007
Copyright © 2007 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.

, fuerstner@mpi-muelheim.mpg.de

Abstract

Abstract Image

A reaction cascade comprising a rhodium-catalyzed C−H activation, a subsequent hydrometalation of an alkylidene cyclopropane in vicinity, regioselective C−C bond activation of the flanking cyclopropane ring, followed by reductive elimination of the resulting metallacycle, opens a new entry into functionalized cycloheptene derivatives. This crossover of C−H activation and higher order cycloaddition has been performed in two different formats, either using alkylidenecyclopropanes with a lateral vinylpyridine moiety or with a pending aldehyde group as the trigger. The reaction tolerates various functional groups, leaves chiral centers α to the reacting sites unaffected, and proceeds with excellent stereoselectivity. Labeling experiments support the proposed mechanism explaining the observed net cycloisomerization process.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue December 05, 2007
  • Received June 25, 2007

Recommend & Share

Related Content

Other ACS content by these authors: