Rhodium-catalyzed tandem addition/cyclization of bifunctional organoboronate esters to strained alkenes

ORGN 1

Nai-Wen Tseng, ntseng@chem.utoronto.ca, John Mancuso, and Mark Lautens, mlautens@chem.utoronto.ca. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada
Our group has previously explored the synthesis of indanes and indenes utilizing a rhodium-catalyzed tandem cyclization. More recently, we have found that vinylcyclopropanes are produced via an unusual rhodium-catalyzed 1,6-addition of a bifunctional dienylboronate esters to strained alkenes. In addition, cyclopentenes can be formed depending on the substituents on the dienylboronate esters. Preliminary mechanistic studies as well as the reaction scope will be presented.