Catalytic generation of activated carboxylates via N-Heterocyclic carbene-catalyzed redox reactions

ORGN 957

Stephanie S. Sohn, Evelyn L. Rosen, and Jeffrey W. Bode, bode@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106-9510
In the presence of new N-heterocyclic carbene (NHC) organocatalysts, a wide variety of aldehyde substrates undergo redox reactions, leading to catalytically generated activated carboxylates. Reducible groups adjacent to the aldehyde either become protonated or lead to carbon-carbon bond formation. The application of this strategy to the synthesis of esters, thioesters, lactones, and novel carbon–carbon bond forming processes will be described. These operationally friendly reactions of simple starting materials proceed under mild conditions and do not produce byproducts. Investigations into the unique mechanisms of these reactions and their application in asymmetric synthesis will also be presented.

 

New Reactions and Methodology
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

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