4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 35, Pages 12141-12144

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06723

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Funding

  1. Cornell University
  2. Atkinson Center for a Sustainable Future
  3. Cornell Center for Materials Research Shared Facilities from NSF MRSEC [DMR-1120296]

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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.

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