Asymmetric synthesis of diverse cyclopropyl tamoxifen analogs via a rhodium carbenoid transformation and microwave-assisted Suzuki reactions

ORGN 789

Jessica E France, jefrance@acsu.buffalo.edu, Aiwu Ni, and Huw M. L. Davies, hdavies@acsu.buffalo.edu. Department of Chemistry, University at Buffalo, State University of New York, 682 Natural Sciences Complex, Buffalo, NY 14260
The Rh2(S-DOSP)4 catalyzed cyclopropanation of 1-(3-chloropropoxy)-4-vinylbenzene with a novel aryldiazoacetates, containing pinacolboronate ester, was successfully carried out in a highly diastereoselective and enantioselective manner. This cyclopropyl product was manipulated to form the key intermediate, which was further functionalized via a microwave-assisted Suzuki coupling. The resulting cyclopropyl derivatives represent a small library of Tamoxifen analogs that were easily accessed through methodology developed around aryldiazoacetates which incorporate coupling partners.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005