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Volumn 2, Issue 16, 2004, Pages 2267-2269

Nucleophilic trifluoromethylation of cyclic imides using (trifluoromethyl)trimethylsilane CF3SiMe3

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; CONDENSATION; DRUG PRODUCTS; ESTERS; IONS; KETONES; PHYSICAL PROPERTIES;

EID: 4644240741     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b407555b     Document Type: Article
Times cited : (24)

References (40)
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    • 4644277616 scopus 로고    scopus 로고
    • (e) For a recent special issue on "Fluorine in the Life Sciences", see: ChemBioChem, 2004, 5, 557-728.
    • (2004) ChemBioChem , vol.5 , pp. 557-728
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    • Some selected examples: (a) T. Brigaud, O. Lefebvre, R. Plantier-Royon and C. Portella, Tetrahedron Lett., 1996, 37, 6115-6116; (b) R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876; (c) J.-C. Blazejewski, E. Anselmi and M. P. Wilmshurst, Tetrahedron Lett., 1999, 40, 5475-5478; (d) G. K. S. Prakash, M. Mandal and G. A. Olah, Angew. Chem., Int. Ed., 2001, 40, 589-590; (e) D. V. Sevenard, P. Kirsch, G.-V. Röschenthaler, V. N. Movchun and A. A. Kolomeitsev, Synlett, 2001, 379-381; (f) D. V. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G. V. Röschenthaler, Tetrahedron Lett, 2003, 44, 7623-7627.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6115-6116
    • Brigaud, T.1    Lefebvre, O.2    Plantier-Royon, R.3    Portella, C.4
  • 19
    • 0033574485 scopus 로고    scopus 로고
    • Some selected examples: (a) T. Brigaud, O. Lefebvre, R. Plantier-Royon and C. Portella, Tetrahedron Lett., 1996, 37, 6115-6116; (b) R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876; (c) J.-C. Blazejewski, E. Anselmi and M. P. Wilmshurst, Tetrahedron Lett., 1999, 40, 5475-5478; (d) G. K. S. Prakash, M. Mandal and G. A. Olah, Angew. Chem., Int. Ed., 2001, 40, 589-590; (e) D. V. Sevenard, P. Kirsch, G.-V. Röschenthaler, V. N. Movchun and A. A. Kolomeitsev, Synlett, 2001, 379-381; (f) D. V. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G. V. Röschenthaler, Tetrahedron Lett, 2003, 44, 7623-7627.
    • (1999) J. Org. Chem. , vol.64 , pp. 2873-2876
    • Singh, R.P.1    Cao, G.2    Kirchmeier, R.L.3    Shreeve, J.M.4
  • 20
    • 0033165877 scopus 로고    scopus 로고
    • Some selected examples: (a) T. Brigaud, O. Lefebvre, R. Plantier-Royon and C. Portella, Tetrahedron Lett., 1996, 37, 6115-6116; (b) R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876; (c) J.-C. Blazejewski, E. Anselmi and M. P. Wilmshurst, Tetrahedron Lett., 1999, 40, 5475-5478; (d) G. K. S. Prakash, M. Mandal and G. A. Olah, Angew. Chem., Int. Ed., 2001, 40, 589-590; (e) D. V. Sevenard, P. Kirsch, G.-V. Röschenthaler, V. N. Movchun and A. A. Kolomeitsev, Synlett, 2001, 379-381; (f) D. V. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G. V. Röschenthaler, Tetrahedron Lett, 2003, 44, 7623-7627.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5475-5478
    • Blazejewski, J.-C.1    Anselmi, E.2    Wilmshurst, M.P.3
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    • 0035793282 scopus 로고    scopus 로고
    • Some selected examples: (a) T. Brigaud, O. Lefebvre, R. Plantier-Royon and C. Portella, Tetrahedron Lett., 1996, 37, 6115-6116; (b) R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876; (c) J.-C. Blazejewski, E. Anselmi and M. P. Wilmshurst, Tetrahedron Lett., 1999, 40, 5475-5478; (d) G. K. S. Prakash, M. Mandal and G. A. Olah, Angew. Chem., Int. Ed., 2001, 40, 589-590; (e) D. V. Sevenard, P. Kirsch, G.-V. Röschenthaler, V. N. Movchun and A. A. Kolomeitsev, Synlett, 2001, 379-381; (f) D. V. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G. V. Röschenthaler, Tetrahedron Lett, 2003, 44, 7623-7627.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 589-590
    • Prakash, G.K.S.1    Mandal, M.2    Olah, G.A.3
  • 22
    • 0035099869 scopus 로고    scopus 로고
    • Some selected examples: (a) T. Brigaud, O. Lefebvre, R. Plantier-Royon and C. Portella, Tetrahedron Lett., 1996, 37, 6115-6116; (b) R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876; (c) J.-C. Blazejewski, E. Anselmi and M. P. Wilmshurst, Tetrahedron Lett., 1999, 40, 5475-5478; (d) G. K. S. Prakash, M. Mandal and G. A. Olah, Angew. Chem., Int. Ed., 2001, 40, 589-590; (e) D. V. Sevenard, P. Kirsch, G.-V. Röschenthaler, V. N. Movchun and A. A. Kolomeitsev, Synlett, 2001, 379-381; (f) D. V. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G. V. Röschenthaler, Tetrahedron Lett, 2003, 44, 7623-7627.
    • (2001) Synlett , pp. 379-381
    • Sevenard, D.V.1    Kirsch, P.2    Röschenthaler, G.-V.3    Movchun, V.N.4    Kolomeitsev, A.A.5
  • 23
    • 0141741270 scopus 로고    scopus 로고
    • Some selected examples: (a) T. Brigaud, O. Lefebvre, R. Plantier-Royon and C. Portella, Tetrahedron Lett., 1996, 37, 6115-6116; (b) R. P. Singh, G. Cao, R. L. Kirchmeier and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873-2876; (c) J.-C. Blazejewski, E. Anselmi and M. P. Wilmshurst, Tetrahedron Lett., 1999, 40, 5475-5478; (d) G. K. S. Prakash, M. Mandal and G. A. Olah, Angew. Chem., Int. Ed., 2001, 40, 589-590; (e) D. V. Sevenard, P. Kirsch, G.-V. Röschenthaler, V. N. Movchun and A. A. Kolomeitsev, Synlett, 2001, 379-381; (f) D. V. Sevenard, V. Ya. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann and G. V. Röschenthaler, Tetrahedron Lett, 2003, 44, 7623-7627.
    • (2003) Tetrahedron Lett , vol.44 , pp. 7623-7627
    • Sevenard, D.V.1    Ya Sosnovskikh, V.2    Kolomeitsev, A.A.3    Königsmann, M.H.4    Röschenthaler, G.V.5
  • 24
    • 0347931934 scopus 로고    scopus 로고
    • Recent examples: (a) Z. Mincheva, M. Courtois, J. Crèche, M. Rideau and M.-C. Viaud-Massuard, Bioorg. Med. Chem., 2004, 12, 191-197; (b) S. M. Capitosti, T. P. Hansen and M. L. Brown, Bioorg. Med. Chem., 2004, 12, 327-336; (c) A. Leonardi, D. Barlocco, F. Montesano, G. Cignarella, G. Motta, R. Testa, E. Poggesi, M. Seeber, P. G. De Benedetti and F. Fanelli, J. Med. Chem., 2004, 47, 1900-1918; (d) M. L. López-Rodríguez, D. Ayala, A. Viso, B. Benhamú, R. Fernández de la Pradilla, F. Zarza and J. A. Ramos, Bioorg. Med. Chem., 2004, 12, 1551-1557; (e) K. Kuramochi, Y. Mizushina, S. Nagata, F. Sugawara, K. Sakaguchi and S. Kobayashi, Bioorg. Med. Chem., 2004, 12, 1983-1989.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 191-197
    • Mincheva, Z.1    Courtois, M.2    Crèche, J.3    Rideau, M.4    Viaud-Massuard, M.-C.5
  • 25
    • 0347320710 scopus 로고    scopus 로고
    • Recent examples: (a) Z. Mincheva, M. Courtois, J. Crèche, M. Rideau and M.-C. Viaud-Massuard, Bioorg. Med. Chem., 2004, 12, 191-197; (b) S. M. Capitosti, T. P. Hansen and M. L. Brown, Bioorg. Med. Chem., 2004, 12, 327-336; (c) A. Leonardi, D. Barlocco, F. Montesano, G. Cignarella, G. Motta, R. Testa, E. Poggesi, M. Seeber, P. G. De Benedetti and F. Fanelli, J. Med. Chem., 2004, 47, 1900-1918; (d) M. L. López-Rodríguez, D. Ayala, A. Viso, B. Benhamú, R. Fernández de la Pradilla, F. Zarza and J. A. Ramos, Bioorg. Med. Chem., 2004, 12, 1551-1557; (e) K. Kuramochi, Y. Mizushina, S. Nagata, F. Sugawara, K. Sakaguchi and S. Kobayashi, Bioorg. Med. Chem., 2004, 12, 1983-1989.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 327-336
    • Capitosti, S.M.1    Hansen, T.P.2    Brown, M.L.3
  • 26
    • 11144356851 scopus 로고    scopus 로고
    • Recent examples: (a) Z. Mincheva, M. Courtois, J. Crèche, M. Rideau and M.-C. Viaud-Massuard, Bioorg. Med. Chem., 2004, 12, 191-197; (b) S. M. Capitosti, T. P. Hansen and M. L. Brown, Bioorg. Med. Chem., 2004, 12, 327-336; (c) A. Leonardi, D. Barlocco, F. Montesano, G. Cignarella, G. Motta, R. Testa, E. Poggesi, M. Seeber, P. G. De Benedetti and F. Fanelli, J. Med. Chem., 2004, 47, 1900-1918; (d) M. L. López-Rodríguez, D. Ayala, A. Viso, B. Benhamú, R. Fernández de la Pradilla, F. Zarza and J. A. Ramos, Bioorg. Med. Chem., 2004, 12, 1551-1557; (e) K. Kuramochi, Y. Mizushina, S. Nagata, F. Sugawara, K. Sakaguchi and S. Kobayashi, Bioorg. Med. Chem., 2004, 12, 1983-1989.
    • (2004) J. Med. Chem. , vol.47 , pp. 1900-1918
    • Leonardi, A.1    Barlocco, D.2    Montesano, F.3    Cignarella, G.4    Motta, G.5    Testa, R.6    Poggesi, E.7    Seeber, M.8    De Benedetti, P.G.9    Fanelli, F.10
  • 27
    • 1542331577 scopus 로고    scopus 로고
    • Recent examples: (a) Z. Mincheva, M. Courtois, J. Crèche, M. Rideau and M.-C. Viaud-Massuard, Bioorg. Med. Chem., 2004, 12, 191-197; (b) S. M. Capitosti, T. P. Hansen and M. L. Brown, Bioorg. Med. Chem., 2004, 12, 327-336; (c) A. Leonardi, D. Barlocco, F. Montesano, G. Cignarella, G. Motta, R. Testa, E. Poggesi, M. Seeber, P. G. De Benedetti and F. Fanelli, J. Med. Chem., 2004, 47, 1900-1918; (d) M. L. López-Rodríguez, D. Ayala, A. Viso, B. Benhamú, R. Fernández de la Pradilla, F. Zarza and J. A. Ramos, Bioorg. Med. Chem., 2004, 12, 1551-1557; (e) K. Kuramochi, Y. Mizushina, S. Nagata, F. Sugawara, K. Sakaguchi and S. Kobayashi, Bioorg. Med. Chem., 2004, 12, 1983-1989.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 1551-1557
    • López-Rodríguez, M.L.1    Ayala, D.2    Viso, A.3    Benhamú, B.4    De La Pradilla, R.F.5    Zarza, F.6    Ramos, J.A.7
  • 28
    • 1842686948 scopus 로고    scopus 로고
    • Recent examples: (a) Z. Mincheva, M. Courtois, J. Crèche, M. Rideau and M.-C. Viaud-Massuard, Bioorg. Med. Chem., 2004, 12, 191-197; (b) S. M. Capitosti, T. P. Hansen and M. L. Brown, Bioorg. Med. Chem., 2004, 12, 327-336; (c) A. Leonardi, D. Barlocco, F. Montesano, G. Cignarella, G. Motta, R. Testa, E. Poggesi, M. Seeber, P. G. De Benedetti and F. Fanelli, J. Med. Chem., 2004, 47, 1900-1918; (d) M. L. López-Rodríguez, D. Ayala, A. Viso, B. Benhamú, R. Fernández de la Pradilla, F. Zarza and J. A. Ramos, Bioorg. Med. Chem., 2004, 12, 1551-1557; (e) K. Kuramochi, Y. Mizushina, S. Nagata, F. Sugawara, K. Sakaguchi and S. Kobayashi, Bioorg. Med. Chem., 2004, 12, 1983-1989.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 1983-1989
    • Kuramochi, K.1    Mizushina, Y.2    Nagata, S.3    Sugawara, F.4    Sakaguchi, K.5    Kobayashi, S.6
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    • PhD Thesis, University of South Carolina
    • S. Kantamneni, PhD Thesis, University of South Carolina, 1993.
    • (1993)
    • Kantamneni, S.1
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    • note
    • Endo, exo refer to the orientation of the 4-bromophenyl ring at C(4) with respect to the bicyclic perhydropyrrolo[3,4-c]pyrrole scaffold, and cis, trans to the position of this ring with respect to the configuration of C(8a) at the fusion of the two pentagons in the perhydropyrrolizidine bicycle; for the synthesis of this scaffold, see ref. 13.


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