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Volumn 47, Issue 17, 2008, Pages 3238-3241

Enantioselective phase-transfer-catalyzed intramolecular Aza-Michael reaction: Effective route to pyrazino-indole compounds

Author keywords

Asymmetric catalysis; Cyclization; Indoles; Michael addition; Phase transfer catalysis

Indexed keywords

CHEMICAL REACTIONS; CHLORINE COMPOUNDS; KETONES;

EID: 45549106383     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705685     Document Type: Article
Times cited : (156)

References (35)
  • 4
    • 53549086584 scopus 로고    scopus 로고
    • N. Nettekoven, J.-M. Plancher, H. Richter, O. Roche, S. Taylor, PCT Int. Appl. WO US 2007/0135416 A1, 2007.
    • c) N. Nettekoven, J.-M. Plancher, H. Richter, O. Roche, S. Taylor, PCT Int. Appl. WO US 2007/0135416 A1, 2007.
  • 5
    • 53549104574 scopus 로고    scopus 로고
    • J. M. Bentley, P. Hebeisen, M. Muller, H. Richter, S. Roever, P. Mattei, S. Taylor, PCT Int. Appl. WO 2001-EP8520 20010724, 2002;
    • a) J. M. Bentley, P. Hebeisen, M. Muller, H. Richter, S. Roever, P. Mattei, S. Taylor, PCT Int. Appl. WO 2001-EP8520 20010724, 2002;
  • 7
    • 27444436814 scopus 로고    scopus 로고
    • Analogous approaches were employed for the synthesis of pyrrole-based alkaloids: a J. Patel, N. Pelloux-Léon, F. Minassian, Y. Vallée, J. Org. Chem. 2005, 70, 9081-9084;
    • Analogous approaches were employed for the synthesis of pyrrole-based alkaloids: a) J. Patel, N. Pelloux-Léon, F. Minassian, Y. Vallée, J. Org. Chem. 2005, 70, 9081-9084;
  • 11
    • 1042276935 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 550-556;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 550-556
  • 15
    • 4544324311 scopus 로고    scopus 로고
    • For a regioselective racemic Pd-catalyzed approach to N1- and C3-allylic alkylation of indoles, see: M. Bandini, A. Melloni, A. Umani-Ronchi, Org. Lett. 2004, 6, 3199-3202.
    • For a regioselective racemic Pd-catalyzed approach to N1- and C3-allylic alkylation of indoles, see: M. Bandini, A. Melloni, A. Umani-Ronchi, Org. Lett. 2004, 6, 3199-3202.
  • 16
    • 0000528090 scopus 로고    scopus 로고
    • a) A. Nelson, Angew. Chem. 1999, 111, 1685-1687;
    • (1999) Angew. Chem , vol.111 , pp. 1685-1687
    • Nelson, A.1
  • 17
    • 0033152728 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 1583-1585;
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 1583-1585
  • 21
    • 14944358971 scopus 로고    scopus 로고
    • For recent reviews on enantioselective Michael and hetero-Michael reactions, see: a
    • For recent reviews on enantioselective Michael and hetero-Michael reactions, see: a) L.-W. Xu, C.-G. Xia, Eur. J. Org. Chem. 2005, 633-639;
    • (2005) Eur. J. Org. Chem , pp. 633-639
    • Xu, L.-W.1    Xia, C.-G.2
  • 23
    • 34547623607 scopus 로고    scopus 로고
    • and references therein
    • c) H. Pellissier, Tetrahedron 2007, 63, 9267-9331, and references therein.
    • (2007) Tetrahedron , vol.63 , pp. 9267-9331
    • Pellissier, H.1
  • 24
    • 35048891167 scopus 로고    scopus 로고
    • For a review on the synthesis of bioactive molecules through enantioselective organocatalysis, see
    • For a review on the synthesis of bioactive molecules through enantioselective organocatalysis, see: R. Marcia de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575-2600.
    • (2007) Eur. J. Org. Chem , pp. 2575-2600
    • Marcia de Figueiredo, R.1    Christmann, M.2
  • 28
    • 0037191623 scopus 로고    scopus 로고
    • For representative examples of the effect of electron-withdrawing groups on chiral phase-transfer catalysts, see: a S. Jew, M.-S. Yoo, B.-S. Jeong, I. Y. Park, H. Park, Org. Lett. 2002, 4, 4245-4248;
    • For representative examples of the effect of electron-withdrawing groups on chiral phase-transfer catalysts, see: a) S. Jew, M.-S. Yoo, B.-S. Jeong, I. Y. Park, H. Park, Org. Lett. 2002, 4, 4245-4248;
  • 32
    • 53549083422 scopus 로고    scopus 로고
    • Under optimal conditions, the pyrrolyl derivatives underwent cyclization with promising enantiomeric excesses (50-63% ee). However, new specific organocatalysts for this class of compounds are under investigation in our laboratory and will be reported in due course.
    • Under optimal conditions, the pyrrolyl derivatives underwent cyclization with promising enantiomeric excesses (50-63% ee). However, new specific organocatalysts for this class of compounds are under investigation in our laboratory and will be reported in due course.


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