Synthesizing substituted pyrolidines from β-amino radical precursors
USM Professor Prudenté exploits the reactivity of aziridines and aziridinium ions to generate substituted pyrolidines and beta-amino acid derivatives. The pyrolidine and beta-amino acid structural units are found in naturally occurring and synthetic compounds that display antibiotic, antifungal, cytotoxic functions, as well as enzyme inhibition and DNA binding capability. This project, originally supported by the American Chemical Society’s Petroleum Research Fund, is an integral part of the organic laboratory curriculum. Starting with different substrates, students explore various synthetic methodologies aimed at generating substituted aziridines.
- Gail Willette and Caryn Prudenté, "Radical Aziridinum Ions," presented at the 231st ACS National meeting, April 2006
- Laura Fraley and Caryn Prudenté, "Beta-amino Radicals Generated from Single-Electron Reduction of Aziridinium Ions," presented at the 231st ACS National meeting, April 2006