Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 603-613
doi:10.1351/pac200476030603
New methods for the synthesis of heterocyclic compounds*
A. Caiazzo, S. Dalili, C. Picard, M. Sasaki, T. Siu, and A. K. Yudin
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada; Ylektra, Inc., 100 University Ave., 10th Floor, South Tower, Toronto, Ontario M5J 1V6, Canada
Abstract:
Due to frequent occurrence of nitrogen-containing groups among the biologically active compounds, chemoselective functionalization of organic molecules with nitrogen-containing functional groups is an important area of organic synthesis. We have proposed and implemented a new strategy toward design of nitrogen-transfer reactions on inert electrode surfaces with a particular focus on the generation and trapping of highly reactive nitrogen-transfer agents. A wide range of structurally dissimilar olefins can be readily transformed into the corresponding aziridines. The resulting aziridines are precursors to a range of catalysts via nucleophilic ring-opening with diaryl- and dialkyl phosphines. Another strategy explored in the context of oxidative nitrogen transfer is cycloamination of olefins using NH aziridines.