Development of an oxazaborolidine catalyst for alkylation reactions

WCC 10

Robert K. Boeckman Jr. and Rebecca A. Murphy, Department of Chemistry, University of Rochester, P.O. Box 270216 Hutchinson Hall, Rochester, NY 14627-0216
Oxazaborolidines, such as Corey-Bakshi-Shibata reagent (CBS), hold great promise in the context of asymmetric organocatalysis. The use of electrophile activated oxazaborolidine catalysts in tandem with Pd0 catalysis have been shown to perform enantioselective allylic alkylation. Key modifications of the CBS reagent can increase the enantiomeric excess achieved through sterically restricting the axis of approach of the allyl palladium reagents. The system also appears to be able to be converted into a catalytic, rather than stoichiometric reaction through the use of a counterion that liberates the alkylated product and regenerates CBS. If perfected this method would be the first successful method for catalytic enantioselective allylic alkylation as well as a valuable addition to the toolbox of enantioselective methods of alkylation that would be available to modern synthetic chemists in pharmaceutical process chemical industry.

The Merck Index Women in Chemistry
2:30 PM-4:30 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Poster

Women Chemists Committee

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009