Rauhut-Currier-Initiated Organocascade Reaction: Synthesis of Substituted Dispirocyclohexanes through a [2+2+2] Strategy between 2-Arylideneindan-1,3-diones and Activated Alkenes

Yi Ya Zhang, Ramani Gurubrahamam, Kwunmin Chen

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11 Citations (Scopus)


For the synthesis of multisubstituted dispirocyclohexane derivatives, a Rauhut-Currier-initiated organocascade reaction between 2-arylideneindan-1,3-diones and activated alkenes in the presence of diazabicyclo[2.2.2]octane (DABCO) was demonstrated. The functionalized dispirocyclohexanes with a wide range of substituents were obtained in satisfactory to excellent chemical yields (58-99%) with high chemo- and diastereoselectivities (>95:5 dr). This organocatalytic reaction proceeded smoothly through Michael/Michael cyclization, which involves the formation of three new carbon-carbon bonds with simultaneous construction of two all-carbon spiro quaternary centers.

Original languageEnglish
Pages (from-to)2457-2463
Number of pages7
JournalAdvanced Synthesis and Catalysis
Issue number11
Publication statusPublished - 2015 Aug 1



  • Michael addition
  • Rauhut-Currier reaction
  • dispirocyclohexanes
  • indan-1,3-diones
  • organocascade
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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