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Volumn 33, Issue 10, 2004, Pages 1354-1355

A new class of substrates for the nucleophilic 5-endo-trig cyclization, 1-trifluoromethyl vinyl compounds: Syntheses of indoline and pyrrolidine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FLUORIDE ION; FLUORINE DERIVATIVE; INDOLE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONE DERIVATIVE; VINYL DERIVATIVE;

EID: 11844296028     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1354     Document Type: Article
Times cited : (35)

References (27)
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    • For a recent report on the intramolecular cyclization of N-acylimimium ions with an aromatic π-nucleophile, see: P. D. Bailey, K. M. Morgan, D. I. Smith, and J. M. Vernon, Tetrahedron, 59, 3369 (2003).
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    • ed. by G. W. Gribble and T. L. Gilchrist, Pergamon, Amsterdam, Chap. 2
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    • Knight, D.W.1
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    • For recent reports, see: a) A. J. Clark, C. P. Dell, J. M. McDonagh, J. Geden, and P. Mawdsley, Org. Lett., 5, 2063 (2003). b) C. Chatgilialoglu, C. Ferreri, M. Guerra, V. Timokhin, G. Froudakis, and T. Gimisis, J. Am. Chem. Soc., 124, 10765 (2002). For recent reviews, see: c) H. Ishibashi, T. Sato, and M. Ikeda, Synthesis, 2002, 695. d) A. F. Parsons, C. R. Acad. Sci, 4, 391 (2001).
    • (2003) Org. Lett. , vol.5 , pp. 2063
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    • For recent reports, see: a) A. J. Clark, C. P. Dell, J. M. McDonagh, J. Geden, and P. Mawdsley, Org. Lett., 5, 2063 (2003). b) C. Chatgilialoglu, C. Ferreri, M. Guerra, V. Timokhin, G. Froudakis, and T. Gimisis, J. Am. Chem. Soc., 124, 10765 (2002). For recent reviews, see: c) H. Ishibashi, T. Sato, and M. Ikeda, Synthesis, 2002, 695. d) A. F. Parsons, C. R. Acad. Sci, 4, 391 (2001).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10765
    • Chatgilialoglu, C.1    Ferreri, C.2    Guerra, M.3    Timokhin, V.4    Froudakis, G.5    Gimisis, T.6
  • 9
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    • For recent reports, see: a) A. J. Clark, C. P. Dell, J. M. McDonagh, J. Geden, and P. Mawdsley, Org. Lett., 5, 2063 (2003). b) C. Chatgilialoglu, C. Ferreri, M. Guerra, V. Timokhin, G. Froudakis, and T. Gimisis, J. Am. Chem. Soc., 124, 10765 (2002). For recent reviews, see: c) H. Ishibashi, T. Sato, and M. Ikeda, Synthesis, 2002, 695. d) A. F. Parsons, C. R. Acad. Sci, 4, 391 (2001).
    • Synthesis , vol.2002 , pp. 695
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    • For recent reports, see: a) A. J. Clark, C. P. Dell, J. M. McDonagh, J. Geden, and P. Mawdsley, Org. Lett., 5, 2063 (2003). b) C. Chatgilialoglu, C. Ferreri, M. Guerra, V. Timokhin, G. Froudakis, and T. Gimisis, J. Am. Chem. Soc., 124, 10765 (2002). For recent reviews, see: c) H. Ishibashi, T. Sato, and M. Ikeda, Synthesis, 2002, 695. d) A. F. Parsons, C. R. Acad. Sci, 4, 391 (2001).
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    • Our concept has been followed by calculation: K. Ando, J. Org. Chem., 69, 4203 (2004).
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    • For a report on 3-trifluoromethylindolines, see: a) I. Rodrigues, D. Bonnet-Delpon, and J.-P. Bégué, J. Org. Chem., 66, 2098 (2001). For reports on 3-trifluoromethylindoles, see: b) J. Chae, T. Konno, T. Ishihara, and H. Yamanaka, Chem. Lett., 2004, 314 and references therein.
    • (2001) J. Org. Chem. , vol.66 , pp. 2098
    • Rodrigues, I.1    Bonnet-Delpon, D.2    Bégué, J.-P.3
  • 18
    • 11844257497 scopus 로고    scopus 로고
    • and references therein
    • For a report on 3-trifluoromethylindolines, see: a) I. Rodrigues, D. Bonnet-Delpon, and J.-P. Bégué, J. Org. Chem., 66, 2098 (2001). For reports on 3-trifluoromethylindoles, see: b) J. Chae, T. Konno, T. Ishihara, and H. Yamanaka, Chem. Lett., 2004, 314 and references therein.
    • Chem. Lett. , vol.2004 , pp. 314
    • Chae, B.J.1    Konno, T.2    Ishihara, T.3    Yamanaka, H.4
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    • note
    • The intermolecular reaction of 5-phenyl-2-trifluoromethyl-1-pentene with N-propyl-p-toluenesulfonamide gave only 2% yield of the corresponding SN2′ product under similar reaction conditions.
  • 24
    • 11844250468 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra with that of 6b.
  • 25
    • 11844292500 scopus 로고    scopus 로고
    • note
    • Under the cyclization conditions, neither the syn nor the anti isomer of 6b underwent syn/anti isomerization.


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