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

Wei Hao, Xiangyu Wu, James Z. Sun, Juno C. Siu, Samantha N. MacMillan and Song Lin*

*Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States, Email: songlincornell.edu

W. Hao, X. Wu, J. Z. Sun, J. C. Siu, S. N. MacMillan, S. Lin, J. Am. Chem. Soc., 2017, 139, 12141-12144.

DOI: 10.1021/jacs.7b06723

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Abstract

Efficient Ti-catalyzed radical formal [3+2] cycloadditions of N-acylaziridines and alkenes provide pyrrolidines 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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proposed mechanism

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Key Words

pyrrolidines

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ID: J48-Y2017