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Catalytic, intramolecular aziridination of alkenes 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 phenyl and benzyl carbamates as starting compounds for an optimized intramolecular N-insertion onto pendant alkenes. These reactions are designed to access benzoxazepine and benzoxazinone molecular scaffolds. 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.
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Atuk, Emin Berk, "Metal Catalyzed, Microwave-Mediated, Intramolecular Aziridination: Synthesis of Benzoxazepine and Benzoxazinone Derivatives" (2015). Senior Projects Spring 2015. 181.
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