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

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• 作者：Sé ; bastien R. Goudreau ; David Marcoux ; André ; B. Charette
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：January 2, 2009
• 年：2009
• 卷：74
• 期：1
• 页码：470-473
• 全文大小：183K
• 年卷期：v.74,no.1(January 2, 2009)
• ISSN：1520-6904

文摘

A general method to access phenyliodonium ylides from malonates has been developed. These ylides provide easy access to a variety of useful 1,1-cyclopropane diesters using rhodium or copper catalysis. 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. This ylide was shown to be a safer and convenient alternative to the corresponding diazo compound and a very efficient way to 1,1-cyclopropane diesters when used with a catalytic amount of Rh₂(esp)₂.