Peptide-catalyzed kinetic resolution of 1,1′-bi-2-naphthol and derivatives

ORGN 159

Elizabeth A. Colby Davie, daviee@bc.edu, Department of Chemistry, Boston College, Merkert Chemistry Center, Chestnut Hill, MA 02467 and Scott J. Miller, scott.miller@yale.edu, Department of Chemistry, Yale University, 225 Prospect Street, P. O. Box 208107, New Haven, CT 06520-8107.
Enantiomerically-enriched 1,1′-bi-2-naphthol (BINOL) has been shown to be a highly effective chiral ligand for a wide variety of enantioselective reactions. The majority of routes to (R) and (S)-BINOL rely on classical chemical resolution or enzymatic resolution methods. We have developed a chemical kinetic resolution of BINOL and related 3,3′-disubstituted derivatives based on peptide-catalyzed group transfer reactions. Identification and optimization of the peptide catalyst will be presented. Additionally, the effects of reagent, substrate structure, and other reaction parameters will be discussed.

 

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