Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles
Cyclisative carbo-iodination of N-alkyl-N-arylacrylamide derivatives (3) in the presence of PhI(OAc)2/I2 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 SN2 reaction.
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Wei, H.-L., Piou, T., Dufour, J., Neuville, L., & Zhu, J. (2011). Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles. Organic Letters, 13(9), 2244–2247. https://doi.org/10.1021/ol2005243
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WOS:000289956700026
2011
13
9
2244
2247
REVIEWED
EPFL