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Volumn 35, Issue 12, 2006, Pages 1376-1377

Rhenium-catalyzed addition of trimethylsilylacetylene to aldimines

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EID: 33847676480     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.1376     Document Type: Article
Times cited : (31)

References (29)
  • 7
    • 0037119338 scopus 로고    scopus 로고
    • For the zinc(II), triethylamine and 2-dimethylaminoethanol-promoted reaction of terminal acetylene with nitrones, see: R. Fässler, D. E. Frantz, J. Oetiker, E. M. Carreira, Angew. Chem., Int. Ed. 2002, 41, 3054.
    • For the zinc(II), triethylamine and 2-dimethylaminoethanol-promoted reaction of terminal acetylene with nitrones, see: R. Fässler, D. E. Frantz, J. Oetiker, E. M. Carreira, Angew. Chem., Int. Ed. 2002, 41, 3054.
  • 12
    • 0037099190 scopus 로고    scopus 로고
    • For the transition metalcatalyzed enantioselective synthesis of propargylamines, see: d
    • For the transition metalcatalyzed enantioselective synthesis of propargylamines, see: d) C. Koradin, K. Polborn, P. Knochel, Angew. Chem., Int. Ed. 2002, 41, 2535.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 2535
    • Koradin, C.1    Polborn, K.2    Knochel, P.3
  • 23
    • 33847620813 scopus 로고    scopus 로고
    • 1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
    • 1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
  • 24
    • 33847623797 scopus 로고    scopus 로고
    • A ketimine, which was derived from the reaction between acetophenone and aniline, did not give the corresponding propargylamine even at 80°C.
    • A ketimine, which was derived from the reaction between acetophenone and aniline, did not give the corresponding propargylamine even at 80°C.
  • 25
    • 0001845650 scopus 로고    scopus 로고
    • For reports that those triflates act as a Lewis acid and activate aldimines, see
    • For reports that those triflates act as a Lewis acid and activate aldimines, see: S. Kobayashi, Top. Organomet. Chem. 1999, 2, 63.
    • (1999) Top. Organomet. Chem , vol.2 , pp. 63
    • Kobayashi, S.1
  • 26
    • 33847681905 scopus 로고    scopus 로고
    • 2. The result indicates that aldimines or propargyl amines did not increase the nucleophilicity of trimethylsilylacetylene (2a) by deprotonation.
    • 2. The result indicates that aldimines or propargyl amines did not increase the nucleophilicity of trimethylsilylacetylene (2a) by deprotonation.
  • 27
    • 0001540726 scopus 로고    scopus 로고
    • For examples of hydride-alkynyl-rhenium complexes, see: a K.-W. Lee, W. T. Pennington, A. W. Cordes, T. L. Brown, J. Am. Chem. Soc. 1985, 107, 631
    • For examples of hydride-alkynyl-rhenium complexes, see: a) K.-W. Lee, W. T. Pennington, A. W. Cordes, T. L. Brown, J. Am. Chem. Soc. 1985, 107, 631.
  • 29
    • 33847685327 scopus 로고    scopus 로고
    • Although the reaction proceeded with only 5.0 mol, of copper(I) chloride, the yield of propargylamine (4) was low 62
    • Although the reaction proceeded with only 5.0 mol % of copper(I) chloride, the yield of propargylamine (4) was low (62%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.