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.
*Plenary and invited lectures presented at the 12th
International Symposium on Organometallic Chemistry Directed Towards
Organic Synthesis (OMCOS-12), Toronto, Ontario, Canada, 6-10 July 2003.
Other lectures are published in this issue, pp.
453-695.
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