title: Rhodium-catalyzed vinylcyclopropanation/cyclopentenation of strained alkenes via a sequential carborhodation process.
abstract: A rhodium-catalyzed reaction of dienylboronate esters with alkenes is described. Strained bicyclic alkenes show the highest reactivity toward the rhodium-catalyzed addition of the dienylboronate esters. Depending on the substitution pattern of dienylboronate esters, an intramolecular 1,6- or 1,4-addition mechanism may be operative, affording carbocycles containing a vinylcyclopropane or cyclopentene moiety.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
authors.forename: Nai-Wen
authors.initials: NW
authors.lastname: Tseng
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D012238:Rhodium
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D003521:Cyclopropanes; D004952:Esters; D012238:Rhodium