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General Method for the Synthesis of Phenyliodonium Ylides from Malonate Esters: Easy Access to 1,1-Cyclopropane Diesters

Sébastien R. Goudreau, David Marcoux and André B. Charette*

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

S. R. Goudreau, D. Marcoux, A. B. Charette, J. Org. Chem., 2009, 74, 470-473.

DOI: 10.1021/jo802208q (free Supporting Information)


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Abstract

Phenyliodonium ylides provide easy access to various 1,1-cyclopropane diesters using rhodium or copper catalysis and are safer and convenient alternatives to the corresponding diazo compounds. Moreover, the iodonium ylide of dimethyl malonate was obtained in 78% yield using improved conditions that involve a simple filtration step to isolate the desired product.

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Key Words

Iodonium Compounds, Phenyliodonium Diacetate, Cyclopropanes


ID: J42-Y2009-0230