Chiral Relay: A Powerful Strategy for Enantioselective Transformations

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This proposal outlines a novel program on 'Chiral Relay' which relies on the use of fluxional groups to impact face selectivity as well as provide reactivity enhancements in a variety of enantioselective transformations. Two novel and powerful methods for controlling stereochemistry - templates and additives - will be exploited by employing them in transformations of significance. Key methodologies to be developed in the proposed work are (1) exo selective Diels-Alder reactions, (2) cycloadditions with alkynoates and alleneimides, (3) enantioselective Friedel-Crafts alkylations, and (4) enantioselective reactions at higher temperatures. The proposed experiments will further our understanding of the interplay between static chirality and fluxional chirality. With this award, the Organic and Macromolecular Chemistry Program is supporting the work of Professor Mukund Sibi, of the Department of Chemistry at North Dakota State University. Professor Sibi and his students are developing methods for the control of the precise three-dimensional placement of atoms in complex organic molecules, using novel methods for the creation and communication of stereochemical information from one part of a molecule to a newly forming portion of the structure. The discovery and development of general methods for the preparation of enantiomerically pure compounds using catalytic processes will benefit society by providing tools for the preparation of important pharmaceutical agents and intermediates.