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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 3
BKCSDE 31(3)
March 20, 2010 

Synthesis of 2,5-Disubstituted Pyrrolidines from N-Alkenyl and Alkynyl N-Benzoyloxysulfonamides Catalyzed by (CuOTf)2C6H6
Wei Min Liu, Zhen Hong Liu, Wei Wen Cheong, Lu Yi Teo Priscilla, Yongxin Li, Koichi Narasaka*
Pyrrolidines, Intramolecular radical cyclization, Copper catalyst, N-Benzoyloxysulfonamides
A new synthetic method of 2,5-disubstituted pyrrolidines is developed by the cyclization of unsaturated N-benzoyloxysulfonamides by (CuOTf)2·C6H6 in refluxing dichloroethane. Various N-4- and N-5-alkenyl and alkynyl N-benzoyloxysulfonamides 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.
563 - 569
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