Palladium-catalyzed [3+2] cycloaddition of carbon dioxide and trimethylenemethane under mild conditions

ORGN 298

George E. Greco, ggreco@goucher.edu, Brittany L. Gleason, Tiffany A. Lowery, Matthew J. Kier, Lisa B. Hollander, lholland@goucher.edu, Amanda D. Worthy, aworthy@goucher.edu, and Shoshanah A. Gibbs. Department of Chemistry, Goucher College, 1021 Dulaney Valley Road, Baltimore, MD 21204
We have recently developed a palladium-catalyzed [3+2] cycloaddition between carbon dioxide and trimethylenemethane which takes place under mild conditions (1 atmosphere of pressure and 50-75 degrees). The Pd-TMM complex must be generated from 2-(acetoxymethyl)-3-(trimethylsilyl)propene or the appropriate substituted derivative. Experiments that probe the scope, regioselectivity, and mechanism of this process will be presented along with some interesting related reactions.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Monday, August 20, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007