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Volumn 11, Issue 6, 2009, Pages 1237-1240

Intramolecular carbolithiation reactions for the synthesis of 2,4-disubstituted tetrahydro-quinolines: Evaluation of TMEDA and (-)-sparteine as ligands in the stereoselectivity

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EID: 64349122907     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900066c     Document Type: Article
Times cited : (30)

References (67)
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    • The procedure has also been extended to the corresponding alkyne derivatives; see, for instance
    • (g) Sanz, R.; Ignacio, J.; Rodríguez, M. A.; Fañańas, F. J.; Barluenga, J. Chem.-Eur. J. 2007, 13, 4998-5008. The procedure has also been extended to the corresponding alkyne derivatives; see, for instance:
    • (2007) Chem.-Eur. J , vol.13 , pp. 4998-5008
    • Sanz, R.1    Ignacio, J.2    Rodríguez, M.A.3    Fañańas, F.J.4    Barluenga, J.5
  • 15
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    • Rappoport, Z., Marek, I., Eds. The Chemistry of Organolithium Compounds: Patai Series: The Chemistry of Functional Groups, 1; Rappoport, Z., Ed.; Wiley: Chichester, 2004.
    • (b) Rappoport, Z., Marek, I., Eds. The Chemistry of Organolithium Compounds: Patai Series: The Chemistry of Functional Groups, Vol. 1; Rappoport, Z., Ed.; Wiley: Chichester, 2004.
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    • For some representative examples, see: Indoles: (a) Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F. J. J. Am. Chem. Soc. 1998, 120, 4865-4866. Indolines:
    • For some representative examples, see: Indoles: (a) Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F. J. J. Am. Chem. Soc. 1998, 120, 4865-4866. Indolines:
  • 41
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    • For representative examples of our synthetic work in this area, see: a
    • For representative examples of our synthetic work in this area, see: (a) Ruiz, J.; Sotomayor, N.; Lete, E. Org. Lett. 2003, 5, 1115-1117.
    • (2003) Org. Lett , vol.5 , pp. 1115-1117
    • Ruiz, J.1    Sotomayor, N.2    Lete, E.3
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    • Gray, M.; Tinkl, M.; Snieckus, V. In ComprehensiVe Organomet al.lic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Exeter, 1995; 11, pp 66-92.
    • (b) Gray, M.; Tinkl, M.; Snieckus, V. In ComprehensiVe Organomet al.lic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Exeter, 1995; Vol. 11, pp 66-92.
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    • See also ref 1
    • See also ref 1.
  • 53
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    • All attempts to prepare 2b by quenching the addition reaction with MeI failed.
    • All attempts to prepare 2b by quenching the addition reaction with MeI failed.
  • 54
    • 64349092697 scopus 로고    scopus 로고
    • Attempts to introduce the electron withdrawing group directly on 2b by cross metatethesis with acryl amides in the presence of 1st and 2nd generation Grubbs' catalysts failed, leading only to dimeric product derived from 2b. Besides, addition of functionalized allyl organomagnesium reagents to imine 1 also faliled.
    • Attempts to introduce the electron withdrawing group directly on 2b by cross metatethesis with acryl amides in the presence of 1st and 2nd generation Grubbs' catalysts failed, leading only to dimeric product derived from 2b. Besides, addition of functionalized allyl organomagnesium reagents to imine 1 also faliled.
  • 55
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    • See, for instance refs 2c, g, 5b, and 9
    • See, for instance refs 2c, g, 5b, and 9.
  • 58
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    • The addition of TMEDA has been reported to influence not only the rate of the carbolithiation, but also the stereochemical outcome. See
    • The addition of TMEDA has been reported to influence not only the rate of the carbolithiation, but also the stereochemical outcome. See, for instance: Bailey, W. F.; Jiang, X. Tetrahedron 2005, 61, 3183-3194.
    • (2005) Tetrahedron , vol.61 , pp. 3183-3194
    • for instance1    Bailey, W.F.2    Jiang, X.3
  • 62
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    • Rappoport, Z, Marek, I, Eds, John Wiley and Sons: New York, Chapter 17, p
    • (d) Hoppe, D.; Christoph, G. In The Chemistry of Organo-lithiums Compunds; Rappoport, Z., Marek, I., Eds.; John Wiley and Sons: New York, 2004; Chapter 17, p 1055.
    • (2004) The Chemistry of Organo-lithiums Compunds , pp. 1055
    • Hoppe, D.1    Christoph, G.2
  • 65
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    • The enantiomeric excess for each diastereomer was determined by comparison with the racemic mixture in all cases by CSP HPLC
    • The enantiomeric excess for each diastereomer was determined by comparison with the racemic mixture in all cases by CSP HPLC
  • 66
    • 64349115600 scopus 로고    scopus 로고
    • (Chirlacel OJ, 2% hexane/i-propanol). See Supporting Information.
    • (Chirlacel OJ, 2% hexane/i-propanol). See Supporting Information.
  • 67
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    • The absolute configuration of each diastereomer was assigned by comparison with the results obtained performing the carbolithiation reaction with a substrate that incorporates a R, 4-phenyl-2-oxazolidinone as chiral auxiliary. See Supporting Information
    • The absolute configuration of each diastereomer was assigned by comparison with the results obtained performing the carbolithiation reaction with a substrate that incorporates a (R) - (-) -4-phenyl-2-oxazolidinone as chiral auxiliary. See Supporting Information.


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