Iodo-carbocyclization of electron-deficient alkenes: synthesis of oxindoles and spirooxindoles. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2011

Iodo-carbocyclization of electron-deficient alkenes: synthesis of oxindoles and spirooxindoles.

Hai-Long Wei
  • Fonction : Auteur
Tiffany Piou
  • Fonction : Auteur
Jeremy Dufour
  • Fonction : Auteur
Luc Neuville

Résumé

Cyclisative carbo-iodination of N-alkyl-N-arylacrylamide derivatives (3) in the presence of PhI(OAc)(2)/I(2) afforded functionalized 3-(iodomethyl)-3-substituted-indolin-2-ones (4) in good to excellent yields. With a suitably functionalized linear amide, spirooxindole 8 was prepared in a one-pot fashion via a sequence of iodo-arylation followed by an in situ base-promoted intramolecular S(N)2 reaction.

Domaines

Chimie organique
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Dates et versions

hal-00605871 , version 1 (04-07-2011)

Identifiants

Citer

Hai-Long Wei, Tiffany Piou, Jeremy Dufour, Luc Neuville, Jieping Zhu. Iodo-carbocyclization of electron-deficient alkenes: synthesis of oxindoles and spirooxindoles.. Organic Letters, 2011, 13 (9), pp.2244-2247. ⟨10.1021/ol2005243⟩. ⟨hal-00605871⟩
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