4 years ago

Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes

Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes
Xiangyu Wu, James Z. Sun, Samantha N. MacMillan, Wei Hao, Juno C. Siu, Song Lin
We report Ti-catalyzed radical formal [3+2] cycloadditions of N-acylaziridines and alkenes. This method provides an efficient approach to the synthesis of pyrrolidines, structural units prevalent in bioactive compounds and organocatalysts, from readily available starting materials. The overall redox-neutral reaction was achieved via a redox-relay mechanism, which harnesses radical intermediates for selective C—N bond cleavage and formation.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06723

DOI: 10.1021/jacs.7b06723

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