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Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N'-dioxide/Mg super(II) catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields wit... Full description

Journal Title: Angewandte Chemie (International Edition) Mar 2015, Vol.54(13), pp.4032-4035
Main Author: Zhao, Xiaohu
Other Authors: Liu, Xiaohua , Mei, Hongjiang , Guo, Jing , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201410814
Link: http://search.proquest.com/docview/1701043857/?pq-origsite=primo
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title: Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines
format: Article
creator:
  • Zhao, Xiaohu
  • Liu, Xiaohua
  • Mei, Hongjiang
  • Guo, Jing
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Indoles
  • Alkylidene
  • Derivatives
  • Construction
  • Asymmetry
  • Catalysts
  • Cascades
  • Friedel-Crafts Reaction
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Angewandte Chemie (International Edition), Mar 2015, Vol.54(13), pp.4032-4035
description: A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N'-dioxide/Mg super(II) catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction. De-aromatically: A highly efficient dearomatization of 2-isocyanoethylindole derivatives with alkylidene malonates by the title reaction has been developed. With easily available chiral N,N'-dioxide/Mg super(II) complex catalysts, fused polycyclic indolines and spiroindolines were afforded in moderate to excellent yield, excellent diastereo- and enantioselectivity. Tf=trifluoromethanesulfonyl.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201410814
fulltext: fulltext
issn:
  • 14337851
  • 1433-7851
  • 15213773
  • 1521-3773
url: Link


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titleAsymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines
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descriptionA highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N'-dioxide/Mg super(II) catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction. De-aromatically: A highly efficient dearomatization of 2-isocyanoethylindole derivatives with alkylidene malonates by the title reaction has been developed. With easily available chiral N,N'-dioxide/Mg super(II) complex catalysts, fused polycyclic indolines and spiroindolines were afforded in moderate to excellent yield, excellent diastereo- and enantioselectivity. Tf=trifluoromethanesulfonyl.
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descriptionA highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N'-dioxide/Mg super(II) catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction. De-aromatically: A highly efficient dearomatization of 2-isocyanoethylindole derivatives with alkylidene malonates by the title reaction has been developed. With easily available chiral N,N'-dioxide/Mg super(II) complex catalysts, fused polycyclic indolines and spiroindolines were afforded in moderate to excellent yield, excellent diastereo- and enantioselectivity. Tf=trifluoromethanesulfonyl.
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titleAsymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines
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abstractA highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N'-dioxide/Mg super(II) catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction. De-aromatically: A highly efficient dearomatization of 2-isocyanoethylindole derivatives with alkylidene malonates by the title reaction has been developed. With easily available chiral N,N'-dioxide/Mg super(II) complex catalysts, fused polycyclic indolines and spiroindolines were afforded in moderate to excellent yield, excellent diastereo- and enantioselectivity. Tf=trifluoromethanesulfonyl.
doi10.1002/anie.201410814
urlhttp://search.proquest.com/docview/1701043857/
date2015-03-23