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Synthesis 2009(20): 3443-3448
DOI: 10.1055/s-0029-1216970
DOI: 10.1055/s-0029-1216970
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCerium(III) Chloride Heptahydrate-Lithium Iodide: A Novel Reagent System for the Synthesis of N-Arylpyrrolidines
Further Information
Received
25 May 2009
Publication Date:
28 August 2009 (online)
Publication History
Publication Date:
28 August 2009 (online)

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