Nickel-catalyzed rearrangements of vinylcyclopropanes and cyclopropylen-ynes

ORGN 403

Gang Zuo and Janis Louie, Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112-0850
A mild and general route for preparing cyclopentenes through the rearrangement of vinylcyclopropanes (VCPs) is described. Excellent yields of cyclopentenes are obtained using catalytic amounts of Ni(COD)2 and an N-heterocyclic carbene (NHC) ligand at ambient temperature. In addition, when an alkynyl substituent is tethered to the VCP, three different carbocycles (cyclopentane- or cycloheptene-based) are observed. Cyclopentane-based products can be prepared selectively by the judicious choice of NHC ligand (Equation 1).


Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005