Enantioselective CC bond formation by rhodium-catalyzed [2,3] sigmatropic rearrangement between donor/acceptor carbenoids and allylic alcohols

ORGN 705

Zhanjie Li and Huw M. L. Davies, hmdavie@emory.edu. Department of Chemistry, Emory University, 440 Atwood Hall, 1515 Dickey Drive, Atlanta, GA 30322
Metal carbenoids tend to react very effectively with alcohols to generate the OH insertion products. We have recently discovered that donor/acceptor carbenoids react with allylic alcohols to form the products derived from an intermolecular oxonium ylide formation followed by a [2,3]-sigmatropic rearrangement occurred. The full scope of this chemistry will be described.

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

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