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Volumn 10, Issue 18, 2008, Pages 4037-4040

Preference of β-lactam formation in Cu(I)-catalyzed intramolecular coupling of amides with vinyl bromides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BETA LACTAM; COPPER; VINYL BROMIDE; VINYL DERIVATIVE;

EID: 55949118152     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801545a     Document Type: Article
Times cited : (53)

References (52)
  • 1
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    • For selected reviews, see: a, Bruggink, A, Ed, Kluwer: Dordrecht, Netherlands
    • For selected reviews, see: (a) Synthesis of β-Lactam Antibiotics; Bruggink, A., Ed.; Kluwer: Dordrecht, Netherlands, 2001.
    • (2001) Synthesis of β-Lactam Antibiotics
  • 3
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    • Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Pergamon: New York, Chapters 1.18-1.20
    • (c) Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 1B, Chapters 1.18-1.20.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1 B
  • 28
    • 51649112680 scopus 로고    scopus 로고
    • For the latest examples of copper-catalyzed N-vinylation, see:(a) Jiang, B.; Tian, H.; Huang, Z.-G.; Xu, M. Org. Lett. 2008, 10, 2737.
    • For the latest examples of copper-catalyzed N-vinylation, see:(a) Jiang, B.; Tian, H.; Huang, Z.-G.; Xu, M. Org. Lett. 2008, 10, 2737.
  • 44
    • 0024490417 scopus 로고    scopus 로고
    • Joyeau et al. reported the formation of β-lactams via the treatment of 3-bromo-3-butenamides with copper metal (5 equiv) in DMF at 130-135 °C. See: Joyeau, R.; Kobaiter, R.; Sadet, J.; Wakselman, M. Tetrahedron Lett. 1989, 30, 337.
    • Joyeau et al. reported the formation of β-lactams via the treatment of 3-bromo-3-butenamides with copper metal (5 equiv) in DMF at 130-135 °C. See: Joyeau, R.; Kobaiter, R.; Sadet, J.; Wakselman, M. Tetrahedron Lett. 1989, 30, 337.
  • 45
    • 0037178121 scopus 로고    scopus 로고
    • N,N′-Dimethylethylenediamine: Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
    • N,N′-Dimethylethylenediamine: Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
  • 46
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    • 1, 10-Phenanthroline: Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
    • 1, 10-Phenanthroline: Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
  • 48
    • 0141854366 scopus 로고    scopus 로고
    • L-Proline: Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
    • L-Proline: Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
  • 49
    • 0242543883 scopus 로고    scopus 로고
    • N,N-Dimethylglycine hydrochloride: Ma. D.; Cai, Q. Org. Lett. 2003, 5, 3799.
    • N,N-Dimethylglycine hydrochloride: Ma. D.; Cai, Q. Org. Lett. 2003, 5, 3799.
  • 50
    • 33750623389 scopus 로고    scopus 로고
    • For examples of copper-catalyzed double C-N bond formation, see: (a) Martin, R, Rivero, M. R, Buchwald, S. L. Angew. Chem, Int. Ed. 2006, 45, 7079
    • For examples of copper-catalyzed double C-N bond formation, see: (a) Martin, R.; Rivero, M. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079.
  • 52
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    • References 9f and 9i
    • (c) References 9f and 9i.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.