Studies directed towards the Synthesis of Enantio-enriched a,b-Unsaturated Imidates and their Application in a Cyclic Intermediate [3,3]-Sigmatropic Shift
Summer Collier and Caroline Carter 
Faculty Advisor: D. Deardorff

     The overarching goal of this research is the development of synthetic methodologies that permit facile, enantiocontrolled access to molecules of biological importance, more specifically, imidate (1) derived from enantiomerically pure a,b-unsaturated cynanohydrins. Currently substrates with five different R-groups are under study. Predisposition of 1 to palladium(II) catalyzes the stereospecific rearrangement in a [3,3]-sigmatropic shift to form the related acetamide (2). So far, this reaction has been shown to form only trans double bonds. These novel products, with their multitude of functional groups, offer great versatility as building blocks for pharmaceutical drugs.

Support provided by: American Chemical Society-PRF