title: Improved zinc-catalyzed Simmons-Smith reaction: access to various 1,2,3-trisubstituted cyclopropanes.
abstract: The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.
authors.affiliation: Centre in Green Chemistry and Catalysis, FAS-Department of Chemistry, Université de Montréal , P.O. Box 6128, Station Downtown, Montréal, Québec, Canada , H3C 3J7.
authors.forename: Éric
authors.initials: É
authors.lastname: Lévesque
authors.forename: Sébastien R
authors.initials: SR
authors.lastname: Goudreau
authors.forename: André B
authors.initials: AB
authors.lastname: Charette