Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 1, Pages 470-473Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802208q
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Funding
- NSERC (Canada)
- Canada Research Chair Program
- Canada Foundation for Innovation
- Universite de Montreal
- NSERC
- Manuvie Financial
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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 Rh-2(esp)(2).
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