Mechanistic and stereochemical investigations of palladium-catalyzed intramolecular hydroaminations of unactivated alkenes

ORGN 265

Forrest E. Michael, michael@chem.washington.edu and Brian M. Cochran, brianoi@u.washington.edu. Department of Chemistry, University of Washington, Seattle, WA 98195-1700
A mild and facile Pd-catalyzed intramolecular hydroamination of unactivated alkenes will be presented. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. The formation of hydroamination products rather than oxidative amination products is due to the use of a tridentate ligand on Pd which effectively inhibits beta-hydride elimination. Mechanistic aspects of this transformation and approaches towards enantioselective variants will be discussed.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Monday, 11 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006