Binaphthyl-based bifunctional organocatalyst-promoted enantioselective Michael addition of 1,3-diketones to nitroolefins

ORGN 78

Jian Wang, Hao Li, Liansuo Zu, and Wei Wang, wwang@unm.edu. Department of Chemistry, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001
One of the important Michael addition reactions is the addition of nucleophiles to electron deficient nitroalkenes. In this poster presentation, we would like to report a novel binaphthyl-derived amine thiourea bifunctional organocatalyst, which has been demonstrated to efficiently catalyze Michael addition reactions (using as low as 1 mol% loading) of diketones to nitroalkenes with remarkably high enantioselectivities. Furthermore, these Michael adducts can be conveniently converted into synthetic useful, chiral alpha-substituted-beta-amino acids.
 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006