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Volumn 131, Issue 36, 2009, Pages 12924-12926

Thio FCMA intermediates as strong acyl donors: A general solution to the formation of complex amide bonds

Author keywords

[No Author keywords available]

Indexed keywords

ACYL DONORS; AMIDE BOND; CHEMICAL EQUATIONS; GENERAL SOLUTIONS; ISONITRILES; NEUTRAL CONDITIONS; NOVEL METHODOLOGY; THIOACIDS;

EID: 70349130818     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906005j     Document Type: Article
Times cited : (95)

References (32)
  • 17
    • 70349126109 scopus 로고    scopus 로고
    • note
    • Of course, the resulting formamide can be recycled to amine and isonitrile, thus completing the cycle.
  • 18
    • 70349106663 scopus 로고    scopus 로고
    • note
    • 13C), and high resolution mass spectra. All data are provided in the Supporting Information.
  • 19
    • 70349097054 scopus 로고    scopus 로고
    • note
    • The cognate product, which we don't isolate, is almost certainly the (syn) mono thio anhydride. It seems unlikely (but not impossible) that such an anhydride is performing acylation. The rapidity of our observed acylation in less hindered settings renders such an interpretation highly unlikely.
  • 21
    • 70349156663 scopus 로고    scopus 로고
    • note
    • The electronic depiction suggested in going from 40→38 is not intended to address the issue of timing (concertedness).
  • 22
    • 70349107089 scopus 로고    scopus 로고
    • note
    • The initially low solubility of compound 42 in DCM did not affect the reactivity of this substrate. The reaction efficiently proceeded in DCM, DMF, or DCM/DMF (1:1/v:v) solvent systems without additional base.
  • 24
    • 62449152302 scopus 로고    scopus 로고
    • For reviews describing recent advances in amide bond formation, see: (a)
    • For reviews describing recent advances in amide bond formation, see: (a) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 606
    • Valeur, E.1    Bradley, M.2
  • 32
    • 70349147235 scopus 로고    scopus 로고
    • note
    • While quantitative comparisons are not yet available, we believe that the rate of interdiction relative to rearrangement of the thio FCMA renders it a superior acylating device relative to intermediates arising in carbodiimide methodology.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.