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Beilstein J Org Chem. 2013 Oct 14;9:2097-102. doi: 10.3762/bjoc.9.246. eCollection 2013.

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines.

Author information

  • 1Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium ; Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India.

Abstract

An Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity.

KEYWORDS:

Ugi; alkynes; gold; indoles; multicomponent; spiroindolines

PMID:
24204421
[PubMed]
PMCID:
PMC3817510
Free PMC Article
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