4.5 Article

Indium-Promoted Allylation Reaction of Imino-Isatins in Aqueous Media: Synthesis of Quaternary 3-Aminooxindoles

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 15, Pages 2845-2848

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000141

Keywords

Synthetic methods; Indium; Allylation; Nitrogen heterocycles

Funding

  1. Direccion General de Investigacion - Ministerio de Ciencia e Innovacion (DGI-MICINN) [CTQ2006-10292, CTQ2009-09318]
  2. Universidad Complutense-Banco Santander Central Hispano (UCM-BSCH) [GR58/08]
  3. Comunidad Autonoma de Madrid (CAM) [S2009/PPQ-1752]
  4. Consejo Superior de Investigaciones Cientificas (CSIC)
  5. Ministerio de Ciencia e Innovacion (MICINN)
  6. European Social Fund

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Quaternary 3-amino-2-oxindoles have been obtained via allylation and propargylation reactions of imino-isatins in aqueous media promoted by In and Zn respectively, under Barbier conditions, in good to excellent yields. A quaternary new stereocenter has been formed without hydrolysis of the starting imino-isatin.

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