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Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides

A highly efficient N,N'-dioxide-Ni super(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C--C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enant... Full description

Journal Title: Chemistry: A European Journal October 2015, Vol.21(43), pp.15104-15107
Main Author: Chen, Weiliang
Other Authors: Xia, Yong , Lin, Lili , Yuan, Xiao , Guo, Songsong , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201502448
Link: http://search.proquest.com/docview/1786189046/?pq-origsite=primo
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title: Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
format: Article
creator:
  • Chen, Weiliang
  • Xia, Yong
  • Lin, Lili
  • Yuan, Xiao
  • Guo, Songsong
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Indoles
  • Cycloaddition
  • Oxiranes
  • Asymmetry
  • Catalysts
  • Synthesis
  • Cleavage
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, October 2015, Vol.21(43), pp.15104-15107
description: A highly efficient N,N'-dioxide-Ni super(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C--C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C--C cleavage of oxiranes is accomplished by using a highly efficient N,N'-dioxide-Ni super(II) catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201502448
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleAsymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
creatorChen, Weiliang ; Xia, Yong ; Lin, Lili ; Yuan, Xiao ; Guo, Songsong ; Liu, Xiaohua ; Feng, Xiaoming
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subjectIndoles ; Cycloaddition ; Oxiranes ; Asymmetry ; Catalysts ; Synthesis ; Cleavage ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA highly efficient N,N'-dioxide-Ni super(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C--C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C--C cleavage of oxiranes is accomplished by using a highly efficient N,N'-dioxide-Ni super(II) catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.
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descriptionA highly efficient N,N'-dioxide-Ni super(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C--C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C--C cleavage of oxiranes is accomplished by using a highly efficient N,N'-dioxide-Ni super(II) catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.
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titleAsymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
authorChen, Weiliang ; Xia, Yong ; Lin, Lili ; Yuan, Xiao ; Guo, Songsong ; Liu, Xiaohua ; Feng, Xiaoming
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abstractA highly efficient N,N'-dioxide-Ni super(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C--C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C--C cleavage of oxiranes is accomplished by using a highly efficient N,N'-dioxide-Ni super(II) catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.
doi10.1002/chem.201502448
urlhttp://search.proquest.com/docview/1786189046/
date2015-10-19