Chemical diversity derived from stereoselective additions to nitro olefins

ORGN 263

Eamon Comer, ecomer@bu.edu1, Erin Rohan1, Li Deng, deng@brandeis.edu2, and John A. Porco Jr., porco@bu.edu1. (1) Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 24 Cummington Street, Boston, MA 02215, (2) Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02454
Highly enantioselective and diastereoselective conjugate additions of 2-substituted 1,3–dicarbonyl donors to nitro olefins have been developed using readily available, modified cinchona alkaloids. This strategy allows for the stereocontrolled formation of adjacent quarternary and tertiary stereocenters. Manipulation of these conjugate addition templates to afford an array of diverse and stereoenriched compounds will be described.  This approach achieves high skeletal diversity with access to a range of 5 to 10-membered fused and bridged ring systems.

 

 


 


 

Asymmetric Reactions and Syntheses
8:00 AM-11:40 AM, Monday, 11 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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