Asymmetric catalysis with "simple" alpha-amino acids and their peptides

ORGN 307

Scott J. Miller, scott.miller@yale.edu, Department of Chemistry, Yale University, 225 Prospect Street, P. O. Box 208107, New Haven, CT 06520-8107
We have been exploring reactions that employ alpha-amino acids, and their derived peptides as catalysts for a variety of enantioselective and regioselective processes. Superficially, these catalysts appear to be much less complex than enzymes. Yet, correlations between structures and functions are rarely straightforward. This presentation will describe the discovery and use of peptides containing proteinogenic and non-natural amino acids for a variety of asymmetric bond formations. The connections between catalyst structure and function will be explored in a range of mechanistically distinct reactions. Prospects for generalizations and eventual design of catalysts from first principles will be evaluated. In addition, applications to the selective modification of complex molecules, including biologically active natural products, will be described.