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
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
ID: J24-Y2004-370