Organic letters

Synthesis of cyclic sulfonamides via intramolecular copper-catalyzed reaction of unsaturated iminoiodinanes

P Dauban, RH Dodd

文献索引：Dauban, Philippe; Dodd, Robert H. Organic Letters, 2000 , vol. 2, # 15 p. 2327 - 2329

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被引用次数: 125

摘要

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 CH insertion was observed. The aziridines could be opened by various nucleophiles (methanol, thiophenol, allylmagnesium bromide, ...