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Volumn , Issue 9, 2009, Pages 1034-1036

Novel defluorinative alkylation of trifluoroacetaldehyde N,O-acetal derivatives and its application to multi-component reaction

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EID: 61849133786     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b817599c     Document Type: Article
Times cited : (9)

References (47)
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  • 2
    • 61849142036 scopus 로고    scopus 로고
    • ed. K. Uneyama, Blackwell Publishing Ltd, Oxford, UK
    • Organofluorine Chemistry, ed. K. Uneyama, Blackwell Publishing Ltd., Oxford, UK, 2005;
    • (2005) Organofluorine Chemistry
  • 3
    • 0003907264 scopus 로고
    • eds. J. T. Welch and S. Eswarakrishnan, Wiley, New York
    • Fluorine in Bioorganic Chemistry, eds. J. T. Welch and S. Eswarakrishnan, Wiley, New York, 1991;
    • (1991) Fluorine in Bioorganic Chemistry
  • 4
    • 0003420735 scopus 로고
    • eds. R. Filler and Y. Kobayashi, Elsevier, Amsterdam
    • Biomedicinal Aspects of Fluorine Chemistry, eds. R. Filler and Y. Kobayashi, Elsevier, Amsterdam, 1982.
    • (1982) Biomedicinal Aspects of Fluorine Chemistry
  • 20
    • 0000907169 scopus 로고
    • Selected examples on nuclephilic difluoromethylation reactions, see
    • Selected examples on nuclephilic difluoromethylation reactions, see: O. Kitagawa, T. Taguchi and Y. Kobayashi, Tetrahedron Lett., 1988, 29, 1803;
    • (1988) Tetrahedron Lett , vol.29 , pp. 1803
    • Kitagawa, O.1    Taguchi, T.2    Kobayashi, Y.3
  • 39
    • 0025351608 scopus 로고    scopus 로고
    • For instance, defluorination reaction of trifluoroethyl ethers or trifluoroacetaldehyde O,O-acetals by alkyllithium reagents is well known: J. M. Percy, Tetrahedron Lett., 1990, 31, 3931;
    • For instance, defluorination reaction of trifluoroethyl ethers or trifluoroacetaldehyde O,O-acetals by alkyllithium reagents is well known: J. M. Percy, Tetrahedron Lett., 1990, 31, 3931;
  • 45
    • 61849112080 scopus 로고    scopus 로고
    • 2O quench of the reaction mixture of 1a and n-BuLi, deuterium introduction at difluoromethinic position of 2aa was observed.
    • 2O quench of the reaction mixture of 1a and n-BuLi, deuterium introduction at difluoromethinic position of 2aa was observed.
  • 46
    • 61849104739 scopus 로고    scopus 로고
    • Reaction of 1a with an equimolar amount of n-BuLi gave 2aa in 38% yield with the recovery of 1a in 41%.
    • Reaction of 1a with an equimolar amount of n-BuLi gave 2aa in 38% yield with the recovery of 1a in 41%.
  • 47
    • 61849169382 scopus 로고    scopus 로고
    • We examined the thermal stability of intermediate E by stepwise reaction of 1a, n-BuLi and benzaldehyde. After simple evaporation at room temperature of the reaction mixture of 1a and n-BuLi, treatment of the resultant residue with benzaldehyde in Et2O gave 3a without significant decrease in the product yield. This finding strongly indicates that intermediate E is stable at least at room temperature
    • 2O gave 3a without significant decrease in the product yield. This finding strongly indicates that intermediate E is stable at least at room temperature.


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