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Volumn 12, Issue 21, 2010, Pages 5020-5023

Novel method for synthesizing spiro[4.5]cyclohexadienones through a Pd-catalyzed intramolecular ipso-Friedel-Crafts allylic alkylation of phenols

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXADIENONE; CYCLOHEXENE DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; SPIRO COMPOUND;

EID: 78049517379     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102190s     Document Type: Article
Times cited : (219)

References (57)
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    • For reviews, see
    • For reviews, see
  • 4
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    • For recent representative examples, see
    • For recent representative examples, see
  • 18
    • 78049511388 scopus 로고    scopus 로고
    • For recent representative examples of catalytic asymmetric construction of a spirocenter, see
    • For recent representative examples of catalytic asymmetric construction of a spirocenter, see
  • 27
    • 78049514430 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 32
    • 78049492037 scopus 로고    scopus 로고
    • For examples of catalytic intramolecular Friedel-Crafts-type allylations using aromatic nucleophiles, see
    • For examples of catalytic intramolecular Friedel-Crafts-type allylations using aromatic nucleophiles, see
  • 38
    • 78049495377 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude reaction mixture
    • 1H NMR analysis of the crude reaction mixture.
  • 39
    • 78049500870 scopus 로고    scopus 로고
    • Base-promoted intramolecular alkylation of phenols to form spirocyclohexadienones is a classical transformation. See
    • Base-promoted intramolecular alkylation of phenols to form spirocyclohexadienones is a classical transformation. See
  • 41
    • 0343916681 scopus 로고
    • 2 at room temperature in the absence of Pd catalyst. In contrast, 4a was obtained in good yield when an allyl bromide derivative corresponding to 3a was refluxed in t- BuOH in the presence of KO t -Bu
    • 2 at room temperature in the absence of Pd catalyst. In contrast, 4a was obtained in good yield when an allyl bromide derivative corresponding to 3a was refluxed in t- BuOH in the presence of KO t -Bu
    • (1965) Tetrahedron Lett. , vol.21 , pp. 2183
    • Kropp, P.J.1
  • 42
    • 78049500662 scopus 로고    scopus 로고
    • There might be π-orbital interactions between the electron-deficient cationic π-allylpalladium unit and the electron-rich phenoxide ring in the transition states. Phosphorus ligands with π-acidic properties, such as triphenyl phosphite, could enhance the intramolecular charge transfer interaction, facilitating the carbon-carbon bond formation
    • There might be π-orbital interactions between the electron-deficient cationic π-allylpalladium unit and the electron-rich phenoxide ring in the transition states. Phosphorus ligands with π-acidic properties, such as triphenyl phosphite, could enhance the intramolecular charge transfer interaction, facilitating the carbon-carbon bond formation.
  • 43
    • 78049493555 scopus 로고    scopus 로고
    • For reviews on catalytic asymmetric construction of quaternary stereocenters, see
    • For reviews on catalytic asymmetric construction of quaternary stereocenters, see
  • 47
    • 78049519042 scopus 로고    scopus 로고
    • For examples of asymmetric reactions using 10, see
    • For examples of asymmetric reactions using 10, see
  • 57
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    • 3, the product was obtained in 88% yield (dr ratio = 9.2:1; ee: major diastereomer 87% ee, minor diastereomer 18% ee)
    • 3, the product was obtained in 88% yield (dr ratio = 9.2:1; ee: major diastereomer 87% ee, minor diastereomer 18% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.