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Synlett 1991; 1991(11): 800-802
DOI: 10.1055/s-1991-20881
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Unusual C,N-Dialkylation of α,N-Alkanesulfonamide Dianions: A New Route to Tetrahydro-1,4,3-Oxathiazine 4,4-Dioxides1

Evelyne Grunder-Klotz* , Jean-Daniel Ehrhardt
  • *Laboratoire de Pharmacologie Cardiovasculaire et Rénale, URA 589 CNRS, Université Louis Pasteur, 11 rue Humann, F-6700 Strasbourg, France
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Publication Date:
07 March 2002 (online)

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The reaction of gaseous formaldehyde with N-benzyl benzylsulfonamide dianion, prepared from the corresponding sulfonamide and 2.1 equivalents of butyllithium, has led to the unusual formation of a new tetrahydro-1,4,3-oxathiazine 4,4-dioxide heterocycle substituted at position 5 (7-benzyl-5-phenyltetrahydro-1, 4,3-oxathiazine 4,4-dioxide).