Communication

Palladium-Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides

  1. Hervé Clavier*,
  2. Aymeric Lepronier,
  3. Nathalie Bengobesse-Mintsa,
  4. David Gatineau,
  5. Hélène Pellissier,
  6. Laurent Giordano,
  7. Alphonse Tenaglia,
  8. Gérard Buono*

Article first published online: 1 FEB 2013

DOI: 10.1002/adsc.201200903

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 355, Issue 2-3, pages 403–408, February 11, 2013

Additional Information

How to Cite

Clavier, H., Lepronier, A., Bengobesse-Mintsa, N., Gatineau, D., Pellissier, H., Giordano, L., Tenaglia, A. and Buono, G. (2013), Palladium-Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides. Adv. Synth. Catal., 355: 403–408. doi: 10.1002/adsc.201200903

Author Information

  1. Centrale Marseille, Aix-Marseille Université, CNRS, iSm2 UMR 7313, 13397

*Centrale Marseille, Aix-Marseille Université, CNRS, iSm2 UMR 7313, 13397

Publication History

  1. Issue published online: 7 FEB 2013
  2. Article first published online: 1 FEB 2013
  3. Manuscript Received: 9 OCT 2012

Funded by

  • CNRS
  • ANR. Grant Number: program BLAN07-1 190839
  • Ministère de l′enseignement supérieur et de la recherche

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Keywords:

  • cycloaddition;
  • cyclopropanes;
  • norbornenes;
  • palladium;
  • phosphorus;
  • ynamides

Abstract

An efficient palladium-catalyzed [2+1] cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalladacycles and palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing the preparation of aminomethylenecyclopropanes. The reaction showed general applicability to various functionalized bicyclo[2.2.1]hept-2-enes and ynamides. A chiral phosphapalladacycle was tested to carry out this transformation in an enantioselective fashion.

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