Short Communication

Improved Protocol for the Diastereoselective Cyclopropanation of Alkenes using Geminal Dizinc Carbenoids: A Study on the Effect of Zinc Iodide

  1. Jean-François Fournier,
  2. André B. Charette

Article first published online: 18 MAR 2004

DOI: 10.1002/ejoc.200400029

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2004, Issue 7, pages 1401–1404, April 2004

Additional Information

How to Cite

Fournier, J.-F. and Charette, A. (2004), Improved Protocol for the Diastereoselective Cyclopropanation of Alkenes using Geminal Dizinc Carbenoids: A Study on the Effect of Zinc Iodide. European Journal of Organic Chemistry, 2004: 1401–1404. doi: 10.1002/ejoc.200400029

Author Information

  1. Département de Chimie, Université de Montréal, P. O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada, Fax: (internat.) + 514-343-5900

Publication History

  1. Issue published online: 18 MAR 2004
  2. Article first published online: 18 MAR 2004
  3. Manuscript Received: 15 JAN 2004

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Keywords:

  • Carbenoids;
  • Carbocycles;
  • Zinc;
  • Alkenes;
  • Cycloaddition

Abstract

A mixture of ZnI2, EtZnI·2OEt2 and CHI3 produces a gem-dizinc carbenoid that is an efficient cyclopropanating reagent. The presence of ZnI2 allows for shorter reaction times and cleaner reactions, particularly with less reactive substrates. This modification improves the scope of the reaction and it raises important mechanistic issues about this reaction. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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