Beta-lactams or gamma-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

Jonathan Clayden, Clayden Jonathan, David W Watson, Helliwell Madeleine, Chambers Mark

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Substituted acrylamide derivatives of benzylamine are lithiated alpha to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a beta-electron withdrawing group, 4-exo-trig cyclisation to a beta-lactam. [on SciFinder (R)]
    Original languageEnglish
    Pages (from-to)2582-2583
    JournalChemical Communications
    DOIs
    Publication statusPublished - 2003

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