Synthesis of 2, 5-disubstituted pyrrolidines from N-alkenyl and alkynyl N-Benzoyloxysulfonamides catalyzed by (CuOTf)2 · C 6H6

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Abstract

A new synthetic method of 2, 5-disubstituted pyrrolidines is developed by the cyclization of unsaturated N-benzoyl- oxysulfonamides by (CuOTf) 2-C6H6; in refluxing dichloroethane. Various N-A- and N-5-alkenyl and alkynyl N-benzoyl- oxysulfonamides are cyclized to give pyrrolidines. The cyclization proceeds via addition of sulfonamidoyl radicals to intramolecular unsaturated bonds or allylic hydrogen abstraction with the radical intermediates.

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Liu, W. M., Liu, Z. H., Cheong, W. W., Teo Priscilla, L. Y., Li, Y., & Narasaka, K. (2010). Synthesis of 2, 5-disubstituted pyrrolidines from N-alkenyl and alkynyl N-Benzoyloxysulfonamides catalyzed by (CuOTf)2 · C 6H6. Bulletin of the Korean Chemical Society, 31(3), 563–569. https://doi.org/10.5012/bkcs.2010.31.03.563

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