STEREOCONTROLLED AMINE AND PEPTIDE ANALOG SYNTHESIS

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1. A synthetically practical, single-step procedure for the conversion of allylic selenides to protected allylic amines has been developed. The reaction has been shown to be useful for the preparation of optically active allylic amines. The proposed research seeks to develop a version of this reaction which utilizes a chiral auxiliary for the more convenient, general preparation of optically active allylic amines. Intramolecular variations and a modification for the formation of carbon-carbon bonds are proposed. II. Peptide mimics are of significant utility in bioorganic chemistry. The proposed research seeks to complete the first fully stereocontrolled approach to alkene isosteres of dipeptides, and incorporate these into an analog of the immunodominant site of influenza virus hemagluttin. These analogs will be compared to the native substances as antigens and immunogens. Similarly, several isoteric mimics for a Beta-bend are proposed. These compounds will likewise be synthesized and immunologically tested.