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Synthesis 2009(20): 3443-3448  
DOI: 10.1055/s-0029-1216970
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cerium(III) Chloride Heptahydrate-Lithium Iodide: A Novel Reagent System for the Synthesis of N-Arylpyrrolidines

J. S. Yadav*, B. V. Subba Reddy, G. Narasimhulu, D. Chandrakanth, G. Satheesh
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27193535; e-Mail: yadavpub@iict.res.in;
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Publikationsverlauf

Received 25 May 2009
Publikationsdatum:
28. August 2009 (online)

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Abstract

Aldimines, generated in situ from arylamines and aryl aldehydes, undergo smooth cycloaddition with cyclopropane-1,1-dicarboxylate in the presence of the cerium(III) chloride heptahydrate-lithium iodide reagent system in refluxing acetonitrile under neutral conditions to produce the corresponding N-arylpyrrolidines in good yields with high selectivity.

Key words

cerium(III) reagents - aldimines - cyclopropanedicarboxylate - pyrrolidines - cycloadditions - ring expansion

    References

  • 1 O’Hagan D. Nat. Prod. Rep.  2000,  17:  435 ; and previous reports in this series
    CrossrefSuche in Google Scholar
  • 2a Bhagwat SS. Gude C. Chan K. Tetrahedron Lett.  1996,  37:  4627 
    Suche in Google Scholar
  • 2b Hanessian S. Reinhold U. Saulnier M. Claridge S. Bioorg. Med. Chem. Lett.  1998,  8:  2123 
    Suche in Google Scholar
  • 2c Hansen JJ. Krogsgaard-Larsen P. Med. Res. Rev.  1990,  10:  55 
    Suche in Google Scholar
  • 2d Murphy MM. Schullek JR. Gordon EM. Gallop MA. J. Am. Chem. Soc.  1995,  117:  7029 
    Suche in Google Scholar
  • 2e Shi Z.-C. Zeng C.-M. Lin G.-Q. Heterocycles  1995,  41:  277 
    Suche in Google Scholar
  • 2f Cushman DW. Ondetti MA. Prog. Med. Chem.  1980,  17:  41 
    Suche in Google Scholar
  • 3 Wess G. Urmann M. Sickenberger B. Angew. Chem. Int. Ed.  2001,  40:  3341 
    CrossrefSuche in Google Scholar
  • 4a Kantorowsk EJ. Kurth MJ. Tetrahedron  2000,  56:  4317 
    Suche in Google Scholar
  • 4b Kim S. Yoon J.-Y. Synthesis  2000,  1622 
  • 4c Hoberg JO. Tetrahedron  1998,  54:  12631 
    Suche in Google Scholar
  • 5a Wong HNC. Hon M.-Y. Tse C.-W. Yip Y.-C. Tanko J. Hudlicky T. Chem. Rev.  1989,  89:  165 
    Suche in Google Scholar
  • 5b Danishefsky S. Acc. Chem. Res.  1979,  12:  66 
    Suche in Google Scholar
  • 6a Alper PB. Meyers C. Lerchner A. Siegel DR. Carreira EM. Angew. Chem. Int. Ed.  1999,  38:  3186 
    Suche in Google Scholar
  • 6b Fischer C. Meyers C. Carreira EM. Helv. Chim. Acta  2000,  83:  1175 
    Suche in Google Scholar
  • 6c Meyers C. Carreira EM. Angew. Chem. Int. Ed.  2003,  42:  694 
    Suche in Google Scholar
  • 6d Lerchner A. Carreira EM. J. Am. Chem. Soc.  2002,  124:  14826 
    Suche in Google Scholar
  • 7a Lautens M. Han W. J. Am. Chem. Soc.  2002,  124:  6312 
    Suche in Google Scholar
  • 7b Lautens M. Han W. Liu JH.-C. J. Am. Chem. Soc.  2003,  125:  4028 
    Suche in Google Scholar
  • 8 Bertozzi F. Gustafsson M. Olsson R. Org. Lett.  2002,  4:  3147 
    Suche in Google Scholar
  • 9a Carson CA. Kerr MA. J. Org. Chem.  2005,  70:  8242 
    Suche in Google Scholar
  • 9b Kang Y.-B. Tang Y. Sun X.-L. Org. Biomol. Chem.  2006,  4:  299 
    Suche in Google Scholar
  • 10 Pohlhaus PD. Johnson JS. J. Org. Chem.  2005,  70:  1057 
    CrossrefSuche in Google Scholar
  • 11 Imamoto T. Lanthanides in Organic Synthesis   Academic Press; New York: 1994. 
  • 12a Cappa A. Marcantoni E. Torregiani E. Bartoli G. Bellucci MC. Bosco M. Sambri L. J. Org. Chem.  1999,  64:  5696 
    Suche in Google Scholar
  • 12b Marcantoni E. Nobili F. Bartoli G. Bosco M. Sambri L. Torregiani E. J. Org. Chem.  1997,  62:  4183 
    Suche in Google Scholar
  • 12c Di Dea M. Marcantoni E. Torregiani E. Bartoli G. Bellucci MC. Bosco M. Sambri L. J. Org. Chem.  2000,  65:  2830 
    Suche in Google Scholar
  • 13a Yadav JS. Reddy BVS. Synlett  2000,  1275 
  • 13b Yadav JS. Reddy BVS. Bhaskar Reddy K. Satyanarayana M. Tetrahedron Lett.  2002,  43:  7009 
    Suche in Google Scholar
  • 13c Yadav JS. Reddy BVS. Sathaiah K. Vishnumurthy P. Synlett  2005,  2811 
  • 13d Yadav JS. Reddy BVS. Srinivas M. Padmavani B. Tetrahedron  2004,  60:  3261 
    Suche in Google Scholar