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Volumn 9, Issue 6, 2007, Pages 985-988

Gold(I)-catalyzed isomerization of allenyl carbinol esters: An efficient access to functionalized 1,3-butadien-2-ol esters

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EID: 33947590876     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063031t     Document Type: Article
Times cited : (86)

References (45)
  • 19
    • 33750973639 scopus 로고    scopus 로고
    • For selected recent examples, see: a
    • For selected recent examples, see: (a) Gorin, D. J.; Dube, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 14480-14481.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 14480-14481
    • Gorin, D.J.1    Dube, P.2    Toste, F.D.3
  • 26
    • 33750061955 scopus 로고    scopus 로고
    • For selected recent examples, see: a
    • For selected recent examples, see: (a) Gockel, B.; Krause, N. Org. Lett. 2006, 8, 4485-4488.
    • (2006) Org. Lett , vol.8 , pp. 4485-4488
    • Gockel, B.1    Krause, N.2
  • 34
    • 33947579064 scopus 로고    scopus 로고
    • For related studies dealing with the acid-catalyzed or thermal rearrangement of allenyl carbinol esters into 1,3-butadien-2-ol esters, see: (a) Olsson, L. I, Claesson, A, Bogentof, C. Acta Chem. Scand. 1973, 27, 1629-1636
    • For related studies dealing with the acid-catalyzed or thermal rearrangement of allenyl carbinol esters into 1,3-butadien-2-ol esters, see: (a) Olsson, L. I.; Claesson, A.; Bogentof, C. Acta Chem. Scand. 1973, 27, 1629-1636.
  • 40
  • 42
    • 33947604506 scopus 로고    scopus 로고
    • 13c (in refluxing toluene for 24 h: <5% yield).
    • 13c (in refluxing toluene for 24 h: <5% yield).
  • 44
    • 33947577807 scopus 로고    scopus 로고
    • It was proven that gold catalyst 9 did not isomerize the final dienes because performing the isomerization for a longer time or resubmitting the isolated dienes to the same reaction conditions did not change the Z/E ratios.
    • It was proven that gold catalyst 9 did not isomerize the final dienes because performing the isomerization for a longer time or resubmitting the isolated dienes to the same reaction conditions did not change the Z/E ratios.
  • 45
    • 33947590850 scopus 로고    scopus 로고
    • An alternative mechanism involving the activation of the terminal double bond of the allene moiety may be envisaged
    • An alternative mechanism involving the activation of the terminal double bond of the allene moiety may be envisaged.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.