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Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones

The first example of a N,N'-dioxide-Sc super(III)-catalyzed 1,6-addition of 3-substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3-substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with q... Full description

Journal Title: Chemistry: A European Journal May 2015, Vol.21(21), pp.7709-7712
Main Author: Wang, Zhen
Other Authors: Kang, Tengfei , Yao, Qian , Ji, Jie , Liu, Xiaohua , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201500833
Link: http://search.proquest.com/docview/1786200924/?pq-origsite=primo
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title: Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones
format: Article
creator:
  • Wang, Zhen
  • Kang, Tengfei
  • Yao, Qian
  • Ji, Jie
  • Liu, Xiaohua
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Ketones
  • Asymmetry
  • Catalysts
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, May 2015, Vol.21(21), pp.7709-7712
description: The first example of a N,N'-dioxide-Sc super(III)-catalyzed 1,6-addition of 3-substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3-substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with quaternary stereocenters. In addition, the reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones, achieving excellent regioselectivities and enantioselectivities (up to>99% ee). A highly enantioselective 1,6-addition of 3-substituted oxindoles to linear dienylketones has been developed by using a chiral N,N'-dioxide-scandi um(III) complex. This reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones to give excellent regioselectivities (up to greater than or equal to 95:5 d.r.) and enantioselectivities (up to >99% ee).
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201500833
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleScandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones
creatorWang, Zhen ; Kang, Tengfei ; Yao, Qian ; Ji, Jie ; Liu, Xiaohua ; Lin, Lili ; Feng, Xiaoming
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descriptionThe first example of a N,N'-dioxide-Sc super(III)-catalyzed 1,6-addition of 3-substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3-substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with quaternary stereocenters. In addition, the reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones, achieving excellent regioselectivities and enantioselectivities (up to>99% ee). A highly enantioselective 1,6-addition of 3-substituted oxindoles to linear dienylketones has been developed by using a chiral N,N'-dioxide-scandi um(III) complex. This reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones to give excellent regioselectivities (up to greater than or equal to 95:5 d.r.) and enantioselectivities (up to >99% ee).
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descriptionThe first example of a N,N'-dioxide-Sc super(III)-catalyzed 1,6-addition of 3-substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3-substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with quaternary stereocenters. In addition, the reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones, achieving excellent regioselectivities and enantioselectivities (up to>99% ee). A highly enantioselective 1,6-addition of 3-substituted oxindoles to linear dienylketones has been developed by using a chiral N,N'-dioxide-scandi um(III) complex. This reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones to give excellent regioselectivities (up to greater than or equal to 95:5 d.r.) and enantioselectivities (up to >99% ee).
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titleScandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones
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abstractThe first example of a N,N'-dioxide-Sc super(III)-catalyzed 1,6-addition of 3-substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3-substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with quaternary stereocenters. In addition, the reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones, achieving excellent regioselectivities and enantioselectivities (up to>99% ee). A highly enantioselective 1,6-addition of 3-substituted oxindoles to linear dienylketones has been developed by using a chiral N,N'-dioxide-scandi um(III) complex. This reliable catalyst was found to be effective in the asymmetric 1,6-addition of both delta -unsubstituted and delta -methyl-substituted dienyl ketones to give excellent regioselectivities (up to greater than or equal to 95:5 d.r.) and enantioselectivities (up to >99% ee).
doi10.1002/chem.201500833
urlhttp://search.proquest.com/docview/1786200924/
date2015-05-18