N-Heterocyclic carbene-catalyzed, enantioselective annulations of enals and N-sulfonylimines

ORGN 27

Ming He, mhe@chem.ucsb.edu and Jeffrey W. Bode, bode@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106-9510
α,β-unsaturated aldehydes and N-sulfonylimines undergo direct, N-heterocyclic carbene (NHC) catalyzed annulations to give enantioenriched cis-disubstituted lactams via the intermediacy of catalytically generated homoenolates. Critical to the success of this reaction is the use of novel chiral azolium salts as catalysts. The development, scope, mechanism, and extension of these studies to novel, enantioselective NHC-catalyzed annulations reactions will be reported.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:20 PM, Sunday, 10 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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