title: General method for the synthesis of phenyliodonium ylides from malonate esters: easy access to 1,1-cyclopropane diesters.
abstract: 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).
authors.affiliation: Departement de chimie, Universite de Montreal, P.O. Box 6128, Station Downtown, Montreal, Quebec, Canada H3C 3J7.
authors.forename: Sébastien R
authors.initials: SR
authors.lastname: Goudreau
authors.forename: David
authors.initials: D
authors.lastname: Marcoux
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: 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
chemical_list: D003521:Cyclopropanes; D004952:Esters; D008314:Malonates; D009861:Onium Compounds; C510883:phenyliodonium