Lewis Acid Catalyzed Reactions of Aziridino- Olefins

Electrophilic reactions resulting in the fOImation of new carbon-carbon bonds are important tools in organic synthesis. For example, the acid catalyzed cyciization of epoxy olefins has been well documented, while similar cyciizations 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 cyciization. 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 cabocyclic products as well as competing cyciizations to oxazoline products. ~ R R gR R I Lewis AcidlWOO F1..-----~-~ R+~gR o