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Volumn 72, Issue 4, 2007, Pages 1181-1191

Intermolecular and intramolecular α-amidoalkylation reactions using bismuth triflate as the catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ACYLIMINIUM PRECURSORS; DIASTEREOSELECTIVITY; LEWIS ACIDS; POLYHETEROCYCLIC SYSTEMS;

EID: 33846976199     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062077x     Document Type: Article
Times cited : (80)

References (70)
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    • For recent development of novel Lewis acid catalysts for selective organic reactions in aqueous media, see: Kobayashi, S, Manabe, K. Acc. Chem. Res. 2002, 35, 209-217
    • (a) For recent development of novel Lewis acid catalysts for selective organic reactions in aqueous media, see: Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209-217.
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    • See also recent advances in rare earth-metal triflate catalyzed organic synthesis: i
    • (b) See also recent advances in rare earth-metal triflate catalyzed organic synthesis: (i) Luo, H.; Zhu, L.; Talukdar, A.; Zhang, G.; Mi, X.; Cheng, I.-P.; Wang, P.-G. Mini Rev. Org. Chem. 2005, 2, 546-564.
    • (2005) Mini Rev. Org. Chem , vol.2 , pp. 546-564
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    • (a) For applications of bismuth(III) compounds in organic synthesis, see: Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373-8397.
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    • For bismuth(III) triflate in organic synthesis, see: (i) Gaspard-Iloughmane, H.; Le Roux, C. Eur. J. Org. Chem. 2004, 2517-2532.
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    • For efficient methods for the preparation of bismuth(III) trifluoromethanesulfonate, see: (a) Labrouillère, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J.; Desmurs, J. R. Tetrahedron Lett. 1999, 40, 285-286.
    • For efficient methods for the preparation of bismuth(III) trifluoromethanesulfonate, see: (a) Labrouillère, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J.; Desmurs, J. R. Tetrahedron Lett. 1999, 40, 285-286.
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    • For representative papers in this area from our group, see: a
    • For representative papers in this area from our group, see: (a) Daïch, A.; Marchalín, Š.; Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 9187-9190.
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    • 3BH reduction and one-pot reduction/acetylation processes of the imides, see: (a) Takacs, J. M.; Weidner, J. J. J. Org. Chem. 1994, 59, 6480-6483.
    • 3BH reduction and one-pot reduction/acetylation processes of the imides, see: (a) Takacs, J. M.; Weidner, J. J. J. Org. Chem. 1994, 59, 6480-6483.
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    • 3 was sufficient to catalyze the allylation reaction.
    • 3 was sufficient to catalyze the allylation reaction.
  • 69
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    • Taking into account that 2 equiv of starting materials 3m-o was necessary for the formation of the disulfurs 4m-o, these products may be obtained at maximum efficiency in 50% yields.
    • Taking into account that 2 equiv of starting materials 3m-o was necessary for the formation of the disulfurs 4m-o, these products may be obtained at maximum efficiency in 50% yields.


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