Synthesis of cyclic sulfonamides via intramolecular copper-catalyzed reaction of unsaturated iminoiodinanes |
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Authors: | Dauban P Dodd R H |
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Institution: | Institut de Chimie des Substances Naturelles, C. N. R. S., F-91198 Gif-sur-Yvette, France. philippe.dauban@icsn.cnrs-gif.fr |
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Abstract: | Olefinic primary sulfonamides were treated with iodobenzene diacetate and potassium hydroxide in methanol to give intermediate iminoiodinanes. Catalytic copper(I) or (II) triflate then provided intramolecular nitrene delivery leading to aziridine formation except in one case where a rare copper-catalyzed C-H insertion was observed. The aziridines could be opened by various nucleophiles (methanol, thiophenol, allylmagnesium bromide, benzylamine) to give the corresponding substituted cyclic sulfonamides. |
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