Rhodium-catalyzed vinylcyclopropanation/cyclopentenation of strained alkenes via a sequential carborhodation process.
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.
Tseng
Nai-Wen
NW
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
Lautens
Mark
M
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D012238:Rhodium
D000475:Alkenes; D003517:Cyclopentanes; D003521:Cyclopropanes; D004952:Esters; D012238:Rhodium