Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Published : 2010.03.20
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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.

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References

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