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Volumn , Issue 19, 2007, Pages 3158-3165

Efficient, transition metal mediated, sequential, two- and three-component coupling reactions for the synthesis of highly substituted five-membered ring carbocycles

Author keywords

Arylidenecyclopentanes; Copper iodide; Methylenecyclopentanes; Multicomponent reactions; Palladium; Synthetic design

Indexed keywords


EID: 34447318668     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700197     Document Type: Article
Times cited : (25)

References (40)
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    • For selected references, see:a
    • For selected references, see:a) B. M. Trost, A. B. Pinkerton, J. Org. Chem. 2001, 66, 7714;
    • (2001) J. Org. Chem , vol.66 , pp. 7714
    • Trost, B.M.1    Pinkerton, A.B.2
  • 6
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    • Palladium-catalyzed: N. Monteiro, J. Gore, G. Balme, Tetrahedron 1992, 48, 10103;
    • a) Palladium-catalyzed: N. Monteiro, J. Gore, G. Balme, Tetrahedron 1992, 48, 10103;
  • 7
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    • Molybdenum-catalyzed: F. E. McDonald, T. C. Olson, Tetrahedron Lett. 1997, 38, 7691;
    • b) Molybdenum-catalyzed: F. E. McDonald, T. C. Olson, Tetrahedron Lett. 1997, 38, 7691;
  • 8
    • 0033574477 scopus 로고    scopus 로고
    • Cobalt/light-catalyzed: J.-L. Renaud, C. Aubert, M. Malacria, Tetrahedron 1999, 55, 5113;
    • c) Cobalt/light-catalyzed: J.-L. Renaud, C. Aubert, M. Malacria, Tetrahedron 1999, 55, 5113;
  • 9
    • 1842637760 scopus 로고    scopus 로고
    • Gold(I)-catalyzed: J. Kennedy-Smith, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 4526;
    • d) Gold(I)-catalyzed: J. Kennedy-Smith, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 4526;
  • 10
    • 27644479913 scopus 로고    scopus 로고
    • Rhenium-catalyzed: Y. Kuninobu, A. Kawata, K. Takai, Org. Lett. 2005, 7, 4823;
    • e) Rhenium-catalyzed: Y. Kuninobu, A. Kawata, K. Takai, Org. Lett. 2005, 7, 4823;
  • 11
    • 20444465253 scopus 로고    scopus 로고
    • Nickel(II)-catalyzed: Q. Gao, B.-F. Zheng, J.-H. Li, D. Yang, Org. Lett. 2005, 7, 2185.
    • f) Nickel(II)-catalyzed: Q. Gao, B.-F. Zheng, J.-H. Li, D. Yang, Org. Lett. 2005, 7, 2185.
  • 13
    • 0032560954 scopus 로고    scopus 로고
    • Only a few [4+1] annulation strategies have been reported. For example, see:a J. L. Loebach, D. M. Bennet, R. L. Danheiser, J. Am. Chem. Soc. 1998, 120, 9690;
    • Only a few [4+1] annulation strategies have been reported. For example, see:a) J. L. Loebach, D. M. Bennet, R. L. Danheiser, J. Am. Chem. Soc. 1998, 120, 9690;
  • 20
    • 0036373851 scopus 로고    scopus 로고
    • A similar demethoxycarbonylation was recently observed during a Pd-catalyzed tandem cyclization-coupling reaction of conjugated enynes bearing a methyl cyanoacetate as the nucleophile. See: T. Lomberget, D. Bouyssi, G. Balme, Synlett 2002, 1439
    • A similar demethoxycarbonylation was recently observed during a Pd-catalyzed tandem cyclization-coupling reaction of conjugated enynes bearing a methyl cyanoacetate as the nucleophile. See: T. Lomberget, D. Bouyssi, G. Balme, Synlett 2002, 1439.
  • 38
    • 0035847264 scopus 로고    scopus 로고
    • We have already reported the high efficiency of this Pd0 source in a related cyclisation-coupling reaction; see: M. Bottex, M. Cavicchioli, B. Hartmann, N. Monteiro, G. Balme, J. Org. Chem. 2001, 66, 175
    • 0 source in a related cyclisation-coupling reaction; see: M. Bottex, M. Cavicchioli, B. Hartmann, N. Monteiro, G. Balme, J. Org. Chem. 2001, 66, 175.
  • 40
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    • A subsequent control experiment revealed that treatment of the preformed enolate of 1a with 1 equiv. of NaH with benzyl chloride in THF at 50 °C for 7 h led mainly to the recovery of unreacted substrates.
    • A subsequent control experiment revealed that treatment of the preformed enolate of 1a with 1 equiv. of NaH with benzyl chloride in THF at 50 °C for 7 h led mainly to the recovery of unreacted substrates.


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