Electrophilic reactions resulting in the formation of new carbon-carbon bonds are important tools in organic synthesis. For example, the acid catalyzed cyclization of epoxy olefins has been well documented, while similar cyclizations with aziridines have been largely unexplored. The aim of this project is to develop and demonstrate the formation of a carbocyclic compound from aziridino-olefins utilizing a Lewis acid to catalyze the cyclization. In working toward this goal, a number of aziridino-olefins were synthesized from isoprenoid start materials. These aziridino-olefins were then reacted with both Lewis and protic acids in an attempt to induce cyclization. As a result, we have demonstrated the formation of both the desired carbocyclic products as well as competing cyclizations to oxazoline products.
Tymonko '01, Steven, "Lewis Acid Catalyzed Reactions of Aziridino-Olefins" (2001). Honors Projects. Paper 1.