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Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction

A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in... Full description

Journal Title: Chemistry: A European Journal November 2015, Vol.21(48), pp.17453-17458
Main Author: Lian, Xiangjin
Other Authors: Lin, Lili , Wang, Guojin , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201503276
Link: http://search.proquest.com/docview/1800485538/?pq-origsite=primo
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title: Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction
format: Article
creator:
  • Lian, Xiangjin
  • Lin, Lili
  • Wang, Guojin
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Carbon
  • Asymmetry
  • Catalysts
  • Optical Activity
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, November 2015, Vol.21(48), pp.17453-17458
description: A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99% yield and up to 99%ee under mild reaction conditions. The reaction could be scaled up to a gram-scale with the yield and ee maintained. Based on these experiments and on previous reports, a possible transition state was proposed. Animate you aminations! A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst (see scheme). A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained under mild reaction conditions.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201503276
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleChiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction
creatorLian, Xiangjin ; Lin, Lili ; Wang, Guojin ; Liu, Xiaohua ; Feng, Xiaoming
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subjectCarbon ; Asymmetry ; Catalysts ; Optical Activity ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99% yield and up to 99%ee under mild reaction conditions. The reaction could be scaled up to a gram-scale with the yield and ee maintained. Based on these experiments and on previous reports, a possible transition state was proposed. Animate you aminations! A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst (see scheme). A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained under mild reaction conditions.
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titleChiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction
descriptionA catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99% yield and up to 99%ee under mild reaction conditions. The reaction could be scaled up to a gram-scale with the yield and ee maintained. Based on these experiments and on previous reports, a possible transition state was proposed. Animate you aminations! A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst (see scheme). A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained under mild reaction conditions.
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abstractA catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99% yield and up to 99%ee under mild reaction conditions. The reaction could be scaled up to a gram-scale with the yield and ee maintained. Based on these experiments and on previous reports, a possible transition state was proposed. Animate you aminations! A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst (see scheme). A number of optically active beta -naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained under mild reaction conditions.
doi10.1002/chem.201503276
urlhttp://search.proquest.com/docview/1800485538/
date2015-11-23