Pyrrolidinone-fused cyclohexenones by regioselective dearomatising anionic cyclisation of 2-, 3- or 4-methoxybenzamides

J. Clayden, K. Tchabanenko, S. A. Yasin, M. D. Turnbull

    Research output: Contribution to journalArticlepeer-review

    Abstract

    On treatment with t-BuLi in the presence of HMPA, 2-, 3- or 4-methoxybenzamides (o-, m- or p-anisamides) bearing N-benzyl substituents cyclise with dearomatisation to give methyl dienyl ethers which hydrolyse to give single stereo- and regioisomers of pyrrolidine-fused cyclohexenones. The bicyclic enones are versatile synthetic intermediates which undergo transformations such as stereoselective reduction and conjugate addition, regioselective Baeyer-Villiger oxidation, bromination and hydrogenation.
    Original languageEnglish
    Pages (from-to)302-304
    Number of pages2
    JournalSYNLETT
    Issue number2
    Publication statusPublished - 2001

    Keywords

    • Amide
    • Cyclisation
    • Enone
    • Lithiation
    • Regioselectivity

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