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Highly Stereoselective Conjugate Addition and [alpha]-Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes

The highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N'-dioxides under mild conditions. The thermodynamically unstable Z-olefin derivatives were obtained in excellent yields and high e... Full description

Journal Title: Chemistry: A European Journal June 2013, Vol.19(26), pp.8591-8596
Main Author: Wang, Zhen
Other Authors: Zhang, Zuliang , Yao, Qian , Liu, Xiaohua , Cai, Yunfei , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201300816
Link: http://search.proquest.com/docview/1778008788/?pq-origsite=primo
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title: Highly Stereoselective Conjugate Addition and [alpha]-Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes
format: Article
creator:
  • Wang, Zhen
  • Zhang, Zuliang
  • Yao, Qian
  • Liu, Xiaohua
  • Cai, Yunfei
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Scandium
  • Derivatives
  • Chemical Reactions
  • Asymmetry
  • Substitution Reactions
  • Catalysts
  • Conjugates
  • Carbonyl Compounds
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
  • Acetylenic Substitution
  • Alkynes
  • N,N'-Dioxides
  • Oxindoles
  • Scandium
  • Z Selective
ispartof: Chemistry: A European Journal, June 2013, Vol.19(26), pp.8591-8596
description: The highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N'-dioxides under mild conditions. The thermodynamically unstable Z-olefin derivatives were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities. A highly Z-selective asymmetric conjugate addition of alkynyl carbonyl compounds with 3-substituted oxindoles has been developed by using scandium complexes of chiral N,N'-dioxides (L) under mild conditions. The products were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities (see scheme).
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201300816
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleHighly Stereoselective Conjugate Addition and [alpha]-Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes
creatorWang, Zhen ; Zhang, Zuliang ; Yao, Qian ; Liu, Xiaohua ; Cai, Yunfei ; Lin, Lili ; Feng, Xiaoming
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subjectScandium ; Derivatives ; Chemical Reactions ; Asymmetry ; Substitution Reactions ; Catalysts ; Conjugates ; Carbonyl Compounds ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC) ; Acetylenic Substitution ; Alkynes ; N,N'-Dioxides ; Oxindoles ; Scandium ; Z Selective
descriptionThe highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N'-dioxides under mild conditions. The thermodynamically unstable Z-olefin derivatives were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities. A highly Z-selective asymmetric conjugate addition of alkynyl carbonyl compounds with 3-substituted oxindoles has been developed by using scandium complexes of chiral N,N'-dioxides (L) under mild conditions. The products were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities (see scheme).
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titleHighly Stereoselective Conjugate Addition and [alpha]-Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes
descriptionThe highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N'-dioxides under mild conditions. The thermodynamically unstable Z-olefin derivatives were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities. A highly Z-selective asymmetric conjugate addition of alkynyl carbonyl compounds with 3-substituted oxindoles has been developed by using scandium complexes of chiral N,N'-dioxides (L) under mild conditions. The products were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities (see scheme).
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titleHighly Stereoselective Conjugate Addition and [alpha]-Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes
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abstractThe highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N'-dioxides under mild conditions. The thermodynamically unstable Z-olefin derivatives were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities. A highly Z-selective asymmetric conjugate addition of alkynyl carbonyl compounds with 3-substituted oxindoles has been developed by using scandium complexes of chiral N,N'-dioxides (L) under mild conditions. The products were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities (see scheme).
doi10.1002/chem.201300816
urlhttp://search.proquest.com/docview/1778008788/
date2013-06-24