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

Jean-François Fournier, André B. Charette*

*Département de Chimie, Université de Montréal, P. O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada, Email: andre.charetteumontreal.ca

J.-F. Fournier, A. B. Charette, Eur. J. Org. Chem., 2004, 1401-1404.

DOI: 10.1002/ejoc.200400029

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Abstract

A mixture of ZnI₂, EtZnI·2OEt₂ and CHI₃ produces a gem-dizinc carbenoid that is an efficient cyclopropanating reagent, which shortens reaction times and leads to cleaner reactions, particularly with less reactive substrates. Mechanistic aspects of the reaction are discussed.

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Key Words

Carbenoids, Carbocycles, Zinc, Alkenes, Cycloaddition, Cyclopropanation

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ID: J24-Y2004-370