Asymmetric Synthesis and Reactions of Axially Chiral Amides

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The focus of research is the development of synthetic methodology based on the use of axially chiral anilides. New routes for the preparation of anilides will be studied and new reactions that transfer axial chirality from precursor to product will be developed. Radical cyclizations, additions and hydrogen transfer reactions will make up the initial foci of the work. Further, non-radical reactions such as asymmetric organolithium and organopalladium cyclizations will be studied. The research is designed to advance the understanding of the synthesis, structure (including rotational behavior) and reactions of axially chiral amides in order to expand the synthetic utility of this class of compounds.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Dennis P. Curran of the Department of Chemistry at the University of Pittsburgh. Professor Curran will focus his work on developing methodology for the transfer of chirality of synthetic precursors to new stereocenters in products. The work represents a broad-based study of the structural features and synthetic potential of a novel class of chiral anilides. The methodology has fundamental importance and could lead to the production of novel catalysts, reagents and synthetic intermediates of use to synthetic chemists and, beyond that, to the pharmaceutical industry. The research also provides an appropriate venue for the training of students at the graduate level.