General method for the synthesis of phenyliodonium ylides from malonate esters: easy access to 1,1-cyclopropane diesters.
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).
Goudreau
Sébastien R
SR
Departement de chimie, Universite de Montreal, P.O. Box 6128, Station Downtown, Montreal, Quebec, Canada H3C 3J7.
Marcoux
David
D
Charette
André B
AB
D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D004952:Esters; D008314:Malonates; D009861:Onium Compounds; C510883:phenyliodonium