Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

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
Download PDF
⟨ Previous Next ⟩

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

References

  1. Podichetty, A. K.; Wagner, S.; Schröer, S.; Faust, A.; Schäfers, M.; Schober, O.; Kopka, K.; Haufe, G. J. Med. Chem. 2009, 52, 3484-3495. https://doi.org/10.1021/jm8015014
  2. Venalainen, J. I.; Wallén, E. A.; Poso, A. A.; García-Horsman, J. A.; Mannistö, P. T. J. Med. Chem. 2005, 48, 7093-7095. https://doi.org/10.1021/jm0509187
  3. He, X.; Alian, A.; Stroud, R.; Ortia de Montellano, P. R. J. Med. Chem. 2006, 49, 6308-6323. https://doi.org/10.1021/jm060715y
  4. Zhang, J.; Wang, Q.; Fang, H.; Xu, W. F.; Liu, A. L.; Du, G. H. Bioorg. Med. Chem. 2007, 15, 2749-2758. https://doi.org/10.1016/j.bmc.2007.01.020
  5. Lim, H. J.; RajanBabu, T. V. Org. Lett. 2009, 11, 2924-2927. https://doi.org/10.1021/ol900961m
  6. Rao, W. D.; Chan, P. W. H. Chem.-Eur. J. 2008, 14, 10486-10495. https://doi.org/10.1002/chem.200801242
  7. Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147-3150. https://doi.org/10.1021/ol0264814
  8. Haberli, A.; Leumann, C. J. Org. Lett. 2001, 3, 489-492. https://doi.org/10.1021/ol007029s
  9. Zhang, S. H.; Xu, L.; Miao, L.; Shu, H.; Trudell, M. L. J. Org. Chem. 2007, 72, 3133-3136. https://doi.org/10.1021/jo062532p
  10. Zhang, J. L.; Yang, C. G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798-1799. https://doi.org/10.1021/ja053864z
  11. Hona, T.; Aranishi, E.; Kaneda, K. Org. Lett. 2009, 11, 1857-1859. https://doi.org/10.1021/ol9004239
  12. Tanaka, K.; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2005, 78, 1659-1664. https://doi.org/10.1246/bcsj.78.1659
  13. Tsuritani, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003, 68, 3246-3250. https://doi.org/10.1021/jo034043k
  14. Heuger, G.; Kalsow, S.; Göttlich, R. Eur. J. Org. Chem. 2002, 11, 1848-1854.
  15. Senboku, H.; Hasegawa, H.; Orito, K.; Tokuda, M. Heterocycles 1999, 50 (1), 333-340. https://doi.org/10.3987/COM-98-S(H)56
  16. Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709-2711. https://doi.org/10.1021/ol016310j
  17. Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 9803-9810. https://doi.org/10.1021/ja00026a014
  18. Ciriano, M. V.; Korth, H. G.; Scheppingen, W. B.; Mulder, P. J. Am. Chem. Soc. 1999, 121, 6375-6381. https://doi.org/10.1021/ja9837102
  19. Qu, J. Q.; Katsumata, T.; Satoh, M.; Wada, J.; Masuda, T. Macromolecules 2007, 40, 3136-3144. https://doi.org/10.1021/ma062357e
  20. Aggarwal, V. K.; Lopin, C.; Sandrinelli, F. J. Am. Chem. Soc. 2003, 125, 7596-7601. https://doi.org/10.1021/ja0289088
  21. Sharp, L. A.; Zard, S. Z. Org. Lett. 2006, 8, 831-834. https://doi.org/10.1021/ol052749q
  22. Yoshida, M.; Kitamura, M.; Narasaka, K. Chem. Lett. 2002, 31, 144-145.
  23. Koganemaru, Y.; Kitamura, M.; Narasaka, K. Chem. Lett. 2002, 31, 784-785.
  24. Noack, M.; Gottlich, R. Chem. Commun. 2002, 536-537.
  25. Yoshida, M.; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2003, 76, 2003-2008. https://doi.org/10.1246/bcsj.76.2003
  26. Narasaka, K.; Kitamura, M. ARKIVOC (Gainesville, FL, U. S.) 2006, 245-260.
  27. Hemmerling, M.; Sjöholm, Å.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091-4094. https://doi.org/10.1016/S0957-4166(99)00456-5
  28. Gottlich, R. Synthesis 2000, 11, 1561-1564.
  29. Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095-7021. https://doi.org/10.1016/0040-4020(95)00406-X
  30. Kim, S.; Yeon, K. M.; Yoon, K. S. Tetrahedron: Lett. 1997, 38, 3919-3922. https://doi.org/10.1016/S0040-4039(97)00779-X
  31. Marcotullio, M. C.; Campagna, V.; Sternativo, S.; Costantino, F.; Curini, M. Synthesis 2006, 16, 2760-2766.

Cited by

  1. Cyclization of (2-Alkenylphenyl)carbonyl Compounds to Polycyclic Arenes Catalyzed by Copper(II) Trifluoromethanesulfonate or Trifluoromethanesulfuric Acid vol.95, pp.10, 2012, https://doi.org/10.1002/hlca.201200396
  2. Copper-catalyzed redox-neutral C–H amination with amidoximes vol.12, pp.1, 2014, https://doi.org/10.1039/C3OB41871E
  3. O-Arylation with nitroarenes: metal-catalyzed and metal-free methodologies vol.39, pp.1, 2015, https://doi.org/10.1039/C4NJ01293C
  4. Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles vol.8, pp.8, 2017, https://doi.org/10.1039/C7SC01480E
  5. -2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes vol.34, pp.11, 2016, https://doi.org/10.1002/cjoc.201600380
  6. ChemInform Abstract: Synthesis of 2,5-Disubstituted Pyrrolidines from N-Alkenyl and Alkynyl N-Benzoyloxysulfonamides Catalyzed by (CuOTf)2·C6H6. vol.41, pp.32, 2010, https://doi.org/10.1002/chin.201032119
  7. Diverse N‐Heterocyclic Ring Systems via Aza‐Heck Cyclizations of N‐(Pentafluorobenzoyloxy)sulfonamides vol.128, pp.37, 2010, https://doi.org/10.1002/ange.201605152
  8. Diverse N‐Heterocyclic Ring Systems via Aza‐Heck Cyclizations of N‐(Pentafluorobenzoyloxy)sulfonamides vol.55, pp.37, 2010, https://doi.org/10.1002/anie.201605152