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Synlett 1996; 1996(8): 741-742
DOI: 10.1055/s-1996-5515
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Intramolecular Diels-Alder Reactions of Vinylsulfonamides

Peter Metz* , Dieter Seng, Roland Fröhlich, Birgit Wibbeling
  • *Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany, E-mail metz@uni-muenster.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The vinylsulfonamides 3 of the furan-containing N-benzylamines 2 cyclize at room temperature to give the δ-sultams 4 with high diastereoselectivity. For the vinylsulfonamides 6 featuring a three atom tether connecting the furan and the dienophile moieties, the equilibrium between 6 and the γ-sultam 7 is largely shifted towards 7 for N-benzyl substituted 6c in refluxing toluene.

Diels-Alder reaction - intramolecular - stereoselective - vinylsulfonamides - sultams