高極性反応場を用いるカチオンディールス・アンダー反応の開発と天然物合成への応用  [in Japanese] Development of Cationic Diels-Alder Reaction in Highly Polar Media and Total Syntheses of Natural Products  [in Japanese]

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Abstract

Our longstanding interest in the Diels-Alder reactions led us to examine lithium perchlorate in diethyl ether (LPDE) as a medium for effecting [4 + 2] cycloadditions, despite the general view that the rate of the Diels-Alder reaction is essentially independent of solvent polarity. This article describes an effecient, synthetically useful protocol for the construction carbocyclic systems <I>via</I> intramolecular cationic Diels-Alder reactions of <I>in situ</I>-generated heteroatom-stabilized allyl cations in highly polar media. We also present that use of catalytic acid in LPDE to promote intramolecular Diels-Alder reactions of conformationally restricted substrates possessing terminal dienes results in acid catalyzed migration of the diene prior to [4 + 2] cycloaddition.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(1), 39-49, 2000-01-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008818739
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    4957659
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
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