2,3-Dihydroisoindolones by cyclisation and rearomatisation of lithiated benzamides

Jonathan Clayden, Christel J. Menet

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Lithiation of tertiary aromatic N-benzyl amides generates [α]-amido benzyllithiums which cyclise with dearomatisation to cyclic extended enolates. Rearomatisation by oxidation, or, in the case of methoxy-substituted enolates, elimination, yields 2,3-dihydroisoindoles. Enantiomerically enriched products may be formed either by using a chiral base to lithiate the starting material or by using a chiral starting material. © 2003 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)3059-3062
    Number of pages3
    JournalTetrahedron Letters
    Volume44
    Issue number15
    DOIs
    Publication statusPublished - 7 Apr 2003

    Keywords

    • Asymmetric synthesis and induction (of 2,3-dihydroisoindolones by cyclization and rearomatization of lithiated benzamides); Cyclization (prepn. of 2,3-dihydroisoindolones by cyclization and rearomatization of lithiated benzamides); Aromatization (re-; prepn. of 2,3-dihydroisoindolones by cyclization and rearomatization of lithiated benzamides)

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