Catalytic, intramolecular aziridination of olefines continues to be a popular methodology for the preparation of amine-derived heterocycles. Various transition metal complexes, especially dirhodium complexes, have been reported for their catalytic activities in these reactions. Recent work has shown that metal-catalyzed intramolecular addition of nitrogen to alkenes can be achieved both inter- and intramolecularly with sulfonamides and carbamates. Our research utilizes aryl, and heteroaryl carbamates as starting compounds for an optimized intramolecular N-insertion onto pendant cyclic and acyclic alkenes. We report our recent observations in the synthesis of these aziridines and resultant nucleophilic attack/ring opening. Reaction optimization, mechanistic insights, and the scope and limitations of our methodology are discussed.

Dirhodium-mediated transfer of carbamate-derived nitrenes for aziridination-ring opening: A study on optimization and substrate scope

254th National Meeting (2017)

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