Biomimetic asymmetric catalysis using resin-bound analogs of DMAP

ORGN 154

Tammy K. Chu, ahamindra@berkeley.edu and Ahamindra Jain, ahamindra@berkeley.edu. Department of Chemistry, University of California, Berkeley, 332 Latimer Hall, Mail Code 1460, Berkeley, CA 94720-1460
Biomimetic catalysts for acyl transfer based on resin-bound oligopeptides linked to a potent analog of DMAP have been prepared and evaluated in several reactions. Selectivities of greater than 30:1 for the acylation of racemic substrates have been observed, suggesting that the peptides adopt a planar-chiral structure following activation of the pyridine ring during catalysis.
 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

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