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http://dx.doi.org/10.5012/bkcs.2010.31.03.563

Synthesis of 2,5-Disubstituted Pyrrolidines from N-Alkenyl and Alkynyl N-Benzoyloxysulfonamides Catalyzed by (CuOTf)2･C6H6  

Liu, Wei-Min (Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University)
Liu, Zhen-Hong (Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University)
Cheong, Wei-Wen (Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University)
Priscilla, Lu-Yi Teo (Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University)
Li, Yongxin (Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University)
Narasaka, Koichi (Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.3, 2010 , pp. 563-569 More about this Journal
Abstract
A new synthetic method of 2,5-disubstituted pyrrolidines is developed by the cyclization of unsaturated N-benzoyloxysulfonamides by $(CuOTf)_2{\cdot}C_6H_6$ 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.
Keywords
Pyrrolidines; Intramolecular radical cyclization; Copper catalyst; N-Benzoyloxysulfonamides;
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