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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 603-613

New methods for the synthesis of heterocyclic compounds

Aldo Caiazzo, Shadi 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.