Intermolecular dearomatizing addition of organolithium compounds to n-benzoylamides of 2,2,6,6-tetramethylpiperidine.

Jonathan Clayden, Yann J. Y. Foricher, Ho Kam Lam

    Research output: Contribution to journalArticlepeer-review

    Abstract

    N-Benzoylamides of 2,2,6,6-tetramethylpiperidine are not ortholithiated by organolithium compds. but instead undergo nucleophilic addn. of the organolithium compd. to the arom. ring in the manner of a conjugate addn. The resulting dearomatized enolates may be protonated or alkylated, and yield substituted cyclohexadienes in yields of up to 76%. Deprotection of the piperidine ring is possible under acidic conditions. [on SciFinder (R)]
    Original languageEnglish
    Pages (from-to)3558-3565
    JournalEuropean Journal of Organic Chemistry
    DOIs
    Publication statusPublished - 2002

    Keywords

    • Lithiation (intermol. dearomatizing addn. of organolithium compds. to (benzoyl)tetramethylpiperidine derivs.); Addition reaction (nucleophilic; intermol. dearomatizing addn. of organolithium compds. to (benzoyl)tetramethylpiperidine derivs.); Crystal structure; Molecular structure (of (methoxybenzoyl)tetramethylpiperidine); Aromatization (retro; intermol. dearomatizing addn. of organolithium compds. to (benzoyl)tetramethylpiperidine derivs.)

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