Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides

Victor O. Rogachev, Peter Metz

    Research output: Contribution to journal › Article

    9 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

    Fingerprint

    Cycloaddition Reaction
    Hot Temperature
    Pressure
    Methylene Chloride
    Toluene
    Chlorides
    Chemical activation
    naphthosultone
    furan

    ASJC Scopus subject areas

    • Biochemistry, Genetics and Molecular Biology(all)

    Cite this

    Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides. / Rogachev, Victor O.; Metz, Peter.

    In: Nature Protocols, Vol. 1, No. 6, 01.01.2007, p. 3076-3087.

    Research output: Contribution to journal › Article

    Rogachev, VO & Metz, P 2007, 'Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides', Nature Protocols, vol. 1, no. 6, pp. 3076-3087. https://doi.org/10.1038/nprot.2006.463
    Rogachev VO, Metz P. Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides. Nature Protocols. 2007 Jan 1;1(6):3076-3087. https://doi.org/10.1038/nprot.2006.463
    Rogachev, Victor O. ; Metz, Peter. / Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides. In: Nature Protocols. 2007 ; Vol. 1, No. 6. pp. 3076-3087.
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