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Volumn 129, Issue 45, 2007, Pages 13796-13797

Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: An orthogonal peptide bond forming reaction

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 7 AZABENZOTRIAZOLE; AMIDE; CARBENOID; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 36149000925     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0764052     Document Type: Article
Times cited : (340)

References (34)
  • 8
    • 0001094491 scopus 로고    scopus 로고
    • For a sampling of recent contributions in this area, see: a
    • For a sampling of recent contributions in this area, see: (a) Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196.
    • (1996) J. Org. Chem , vol.61 , pp. 4196
    • Ishihara, K.1    Ohara, S.2    Yamamoto, H.3
  • 24
    • 84931705174 scopus 로고    scopus 로고
    • This reactivity was first described by Wallach, who found that treatment of chloral with aqueous cyanide provides dichloroacetic acid: Wallach, O. Ann. Chem. 1873, 6, 114
    • This reactivity was first described by Wallach, who found that treatment of chloral with aqueous cyanide provides dichloroacetic acid: Wallach, O. Ann. Chem. 1873, 6, 114.
  • 25
    • 20544443754 scopus 로고    scopus 로고
    • Movassaghi has shown that amide products can be obtained from treatment of ester with amino alcohols using N-heterocyclic carbenes. This reactivity has been shown to proceed via an intramolecular O → N acyl transfer to generate the amide. Movassaghi, M, Schmidt, M. A. Org. Lett. 2005, 7, 2453
    • Movassaghi has shown that amide products can be obtained from treatment of ester with amino alcohols using N-heterocyclic carbenes. This reactivity has been shown to proceed via an intramolecular O → N acyl transfer to generate the amide. Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453.
  • 29
    • 22244489435 scopus 로고    scopus 로고
    • Catalytic HOAt and HOBt in ester amidation: Han, C.; Lee, J. P.; Lobkovsky, E.; Porco, J. A. J. Am. Chem. Soc. 2005, 127, 10039.
    • Catalytic HOAt and HOBt in ester amidation: Han, C.; Lee, J. P.; Lobkovsky, E.; Porco, J. A. J. Am. Chem. Soc. 2005, 127, 10039.
  • 30
    • 0028924634 scopus 로고    scopus 로고
    • Cascade catalysis: (a) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943.
    • Cascade catalysis: (a) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943.
  • 33
    • 17444401687 scopus 로고    scopus 로고
    • Concurrent tandem catalysis: Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
    • (d) Concurrent tandem catalysis: Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
  • 34
    • 36148986288 scopus 로고    scopus 로고
    • In the absence of cocatalyst, the reaction generates significant amounts of imine and α-reduced carboxylic acid
    • In the absence of cocatalyst, the reaction generates significant amounts of imine and α-reduced carboxylic acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.