Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides

Victor O. Rogachev, Peter Metz

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    Vinylsulfonamides with a furan, carbocyclic, semicyclic or acyclic 1,3-diene moiety are synthetized via a domino elimination-amidation reaction of 2-chloroethanesulfonyl chloride. Intramolecular Diels-Alder reaction of these vinylsulfonamides with thermal (toluene, 110 °C) or high pressure (dichloromethane, 13 kbar) activation provides efficient access to a range of γ- and δ-sultams following a 2-3 d long synthetic procedure. Enantiopure sultams are readily obtained from N-1-phenylethyl substituted vinylsulfonamides.

    Original languageEnglish
    Pages (from-to)3076-3087
    Number of pages12
    JournalNature Protocols
    Volume1
    Issue number6
    DOIs
    Publication statusPublished - 1 Jan 2007

    ASJC Scopus subject areas

    • Biochemistry, Genetics and Molecular Biology(all)

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