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Volumn 9, Issue 21, 2007, Pages 4199-4202

Enol esters: Versatile substrates for mannich-type multicomponent reactions

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; LACTAM; QUINOLINE DERIVATIVE;

EID: 35548962875     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701717z     Document Type: Article
Times cited : (65)

References (49)
  • 1
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    • For an overview, see: Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005. For recent reviews, see:
    • (a) For an overview, see: Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005. For recent reviews, see:
  • 19
    • 0003417469 scopus 로고
    • For recent reviews of the Mannich reaction, see: a, Trost, B. M, Fleming, I, Eds, Pergamon Press: New York, Chapter 4.1
    • For recent reviews of the Mannich reaction, see: (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Kleinman, E.F.1
  • 21
    • 35548959033 scopus 로고    scopus 로고
    • Kobayashi, S.; Ueno, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Yamamoto, H., Pfaltz, A., Eds.; Springer: Berlin, 2004; Supplement 1.Chapter 29.5.
    • (c) Kobayashi, S.; Ueno, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Yamamoto, H., Pfaltz, A., Eds.; Springer: Berlin, 2004; Supplement 1.Chapter 29.5.
  • 29
    • 35549010503 scopus 로고    scopus 로고
    • Minute amounts of compound A were detected in some experiments NMR and MS evidence
    • Minute amounts of compound A were detected in some experiments (NMR and MS evidence).
  • 30
    • 35248848733 scopus 로고
    • To the best of our knowledge, this is an unreported transformation. For a related process, see
    • To the best of our knowledge, this is an unreported transformation. For a related process, see: Baydar, A. E.; Boyd, G. V.; Monteil, R. L.; Lindley, P. F.; Mahmoud, M. M. Chem. Commun. 1976..650.
    • (1976) Chem. Commun , pp. 650
    • Baydar, A.E.1    Boyd, G.V.2    Monteil, R.L.3    Lindley, P.F.4    Mahmoud, M.M.5
  • 34
    • 0345708168 scopus 로고    scopus 로고
    • For the N-arylation of amides, see
    • (d) For the N-arylation of amides, see: Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 5400
    • Ley, S.V.1    Thomas, A.W.2
  • 37
    • 35549003909 scopus 로고    scopus 로고
    • This ratio of stereoisomers seems to be the usual outcome for this kind of processes. For related results, see refs 3 and 4
    • This ratio of stereoisomers seems to be the usual outcome for this kind of processes. For related results, see refs 3 and 4.
  • 39
    • 35548975633 scopus 로고    scopus 로고
    • In agreement with preliminar calculations (AMI) on the relative stability of cis and trans isomers
    • In agreement with preliminar calculations (AMI) on the relative stability of cis and trans isomers.
  • 40
    • 33947448210 scopus 로고    scopus 로고
    • The corresponding carboxylic acid is described: Buehler, C. A.; Edwards, S. P. J. Am Chem. Soc. 1952, 74, 977.
    • The corresponding carboxylic acid is described: Buehler, C. A.; Edwards, S. P. J. Am Chem. Soc. 1952, 74, 977.
  • 41
    • 33845322646 scopus 로고    scopus 로고
    • Quinoline 5b has previously been described: Alves, M. J.; Azoia, N. G.; Gil Fortes, A. Tetrahedron 2007, 63, 727.
    • Quinoline 5b has previously been described: Alves, M. J.; Azoia, N. G.; Gil Fortes, A. Tetrahedron 2007, 63, 727.
  • 43
    • 0001296532 scopus 로고
    • For a related transformation involving the more reactive Nacyliminium ions, see: a
    • For a related transformation involving the more reactive Nacyliminium ions, see: (a) Katritzky, A. R.; Ignatchenko, A. V.; Lang, H. J. Org. Chem 1995, 60, 4002.
    • (1995) J. Org. Chem , vol.60 , pp. 4002
    • Katritzky, A.R.1    Ignatchenko, A.V.2    Lang, H.3
  • 44
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    • Meester, W. J. N.; van Maarseveen, J. H.; Kirchsteiger, K.; Hermkens, P. H: H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Arkivoc 2004, 122.
    • (b) Meester, W. J. N.; van Maarseveen, J. H.; Kirchsteiger, K.; Hermkens, P. H: H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Arkivoc 2004, 122.
  • 45
    • 35549007451 scopus 로고    scopus 로고
    • In this case, the stereochemical complexity of the resulting double lactam was simplified by the acid-catalyzed isomerization to yield a major trans-trans stereoisomer of unknown relative stereochemistry
    • In this case, the stereochemical complexity of the resulting double lactam was simplified by the acid-catalyzed isomerization to yield a major trans-trans stereoisomer of unknown relative stereochemistry.
  • 47
    • 35549009627 scopus 로고    scopus 로고
    • Approximately 150 000 substances with a 5- or 6-membered ring N-aryl lactam core are listed in SciFinder (2006).
    • Approximately 150 000 substances with a 5- or 6-membered ring N-aryl lactam core are listed in SciFinder (2006).


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