Template Catalysis of the Diels-Alder Reaction

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The Diels-Alder reaction is one of the most powerful carbon-carbon bond forming reactions in chemistry, generating as many as four stereocenters in a single step. A U-shaped template will be developed bearing 2,6-di(acylamino)pyridine and carboxylic acid groups to simultaneously bind maleimide and dienes bearing pendant amino groups in an appropriate orientation for Diels-Alder reaction. By means of enthalpic(hydrogen bonding) and entropic(proximity) effects, the template is anticipated to catalyze the Diels-Alder reaction while controlling the stereo- and regioselectivity. The goals of the research include control of the regioselectivity of reaction of substituted cyclopentadienes, inversion of the natural endo-selectivity of the Diels-Alder reaction, and achievement of enantioselectivity. Emphasis will be placed upon the development of strategies to overcome product inhibition interactions. %%% This award is the starter grant increment of Dr. Nowick's Postdoctoral Research Fellowship in Chemistry in support of his research at the University of California at Irvine. The main thrust of Dr. Nowick's research is the development of a template catalyst to bind suitable diene and dienophile components and catalyze regio-, stereo-, and enantioselective Diels-Alder reactions.