ASYMMETRIC CATALYSIS OF STRECKER AMINO ACID SYNTHESIS

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DESCRIPTION: The principal investigator states that he has recently developed a simple, cyclic dipeptide which effectively catalyzes the Strecker synthesis of the non-proteinogenic alpha-amino acid phenylglycine from benzaldehyde, ammonia and HCN in high yield and extraordinarily high enantiomeric excess and that this proposal details extensions to his work directed at the development of a general method for the asymmetric synthesis of alpha-amino acids and their derivatives, as well as those directed toward an increased understanding of the mechanism of catalysis and the true nature of the species responsible for catalysis. It is indicated that the specific targets detailed in this proposal are: A. Asymmetric synthesis of arylglycine derivatives of biological importance. B. Exploration of alternate methods for the hydrolysis of alpha-amino nitriles to alpha-amino acids. C. Further exploring the scope of substrates allowed. D. Development of asymmetric versions of the Ugi and Passerini reactions. E. Modified catalysts for the synthesis of aliphatic alpha-amino acids. F. Obtaining detailed structural information on the catalytic complex.