Privileged catalysts, reactions, and substrates in asymmetric catalysis

MEDI 147

Eric N. Jacobsen, Department of Chemistry and Chemical Biology, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138
One of the important and intriguing lessons learned over the past several years in asymmetric catalysis is that certain chiral ligand frameworks are useful for an extraordinarily wide range of mechanistically unrelated reactions. These "privileged" ligands serve as useful starting points for discovery of new enantioselective reactions. We are exploring a more subtle and less well-developed extension of this notion: the possibility of privileged catalyst-substrate combinations, where a specific recognition pattern between a chiral catalyst and a core substructure of the substrate leads to both high enantioselectivity and broad generality both with respect to the substituents on the substrate and to the reactions the substrate can undergo. This lecture will describe several examples of such privileged combinations in nucleophile-electrophile reactions, along with a discussion of our efforts to elucidate the basis for the extraordinary generality that is observed.
 

ACS Award in Industrial Chemistry Symposium
8:45 AM-12:00 PM, Monday, March 24, 2003 Convention Center -- La Nourvelle Ballroom C, Oral

Division of Medicinal Chemistry
The 225th ACS National Meeting, New Orleans, LA, March 23-27, 2003