Modular oxazolines as catalysts for enantioselective hetero Diels-Alder reaction

ORGN 15

Sridhar Rajaram and Matthew S. Sigman. Department Of Chemistry, University of Utah, 315, south, 1400 East, Salt Lake city, UT 84112
A metal free approach to a catalytic enantioselective hetero Diels-Alder reaction using hydrogen bonds as the catalytic motif will be presented. The catalyst consists of a rigid oxazoline ring with pendant hydrogen bonding arms. Initial studies indicate that the ligand is effective in catalyzing the cycloaddition between benzaldehyde and diene 1. The ligand has been synthesized using a highly modular approach from simple amino alcohols and amino acids, allowing evaluation of structural analogs. Details on optimization, structure activity relationships, and mechanism will be presented.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- 201A, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004