Date of Submission

Spring 2015

Academic Programs and Concentrations

Chemistry

Project Advisor 1

Emily McLaughlin

Abstract/Artist's Statement

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.

Open Access Agreement

On-Campus only

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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