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

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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
Volume357
Issue number11
DOIs
Publication statusPublished - 2015 Aug 1

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Alkenes
Olefins
Carbon
Cyclization
Derivatives

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Rauhut-Currier-Initiated Organocascade Reaction: Synthesis of Substituted Dispirocyclohexanes through a [2+2+2] Strategy between 2-Arylideneindan-1,3-diones and Activated Alkenes",
abstract = "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.",
keywords = "Michael addition, Rauhut-Currier reaction, dispirocyclohexanes, indan-1,3-diones, organocascade, organocatalysis",
author = "Zhang, {Yi Ya} and Ramani Gurubrahamam and Kwunmin Chen",
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AU - Zhang, Yi Ya

AU - Gurubrahamam, Ramani

AU - Chen, Kwunmin

PY - 2015/8/1

Y1 - 2015/8/1

N2 - 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.

AB - 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.

KW - Michael addition

KW - Rauhut-Currier reaction

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KW - indan-1,3-diones

KW - organocascade

KW - organocatalysis

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