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.


Published in:
Organic Letters, 13, 9, 2244-2247
Year:
2011
Publisher:
American Chemical Society
ISSN:
1523-7060
Keywords:
Laboratories:




 Record created 2011-04-30, last modified 2018-12-03


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