A dearomatizing, thionium ion cyclization for the synthesis of functionalized, azaspirocyclic cyclohexadienones

Caroline Ovens, Nathaniel G. Martin, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (Chemical Equation Presented) Thionium ions, generated by the addition of thiols to N-benzylglyoxamides, undergo a dearomatizing spirocyclization. The alkyl or arylsulfanyl group introduced during the thionium ion cyclization can act as a synthetic handle and a stereochemical control element during modifications of the azaspirocyclic frameworks (RF = CH 2CH2C8F17). © 2008 American Chemical Society.
    Original languageEnglish
    Pages (from-to)1441-1444
    Number of pages3
    JournalOrganic Letters
    Volume10
    Issue number7
    DOIs
    Publication statusPublished - 3 Apr 2008

    Keywords

    • PUMMERER REACTION CHEMISTRY
    • CYCLATIVE-CAPTURE STRATEGY
    • NITROGEN-HETEROCYCLES
    • N-HETEROCYCLES
    • ALKALOIDS
    • LACTAMS
    • OXINDOLES

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