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Catalytic Asymmetric Synthesis of 3-( alpha -Hydroxy- beta -carbonyl) Oxindoles by a Sc super(III)-Catalyzed Direct Aldol-Type Reaction

A direct catalytic asymmetric aldol-type reaction of 3-substituted-2-oxindoles with glyoxal derivatives and ethyl trifluoropyruvate, catalyzed by a chiral N,N'-dioxide-Sc(OTf) sub(3) (Tf=trifluoromethanesulfonyl) complex, has been developed that tolerates a wide range of substrates. The reaction pro... Full description

Journal Title: Chemistry: A European Journal March 2010, Vol.16(12), pp.3736-3742
Main Author: Shen, Ke
Other Authors: Liu, Xiaohua , Zheng, Ke , Li, Wei , Hu, Xiaolei , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.200903471
Link: http://search.proquest.com/docview/1800498834/?pq-origsite=primo
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title: Catalytic Asymmetric Synthesis of 3-( alpha -Hydroxy- beta -carbonyl) Oxindoles by a Sc super(III)-Catalyzed Direct Aldol-Type Reaction
format: Article
creator:
  • Shen, Ke
  • Liu, Xiaohua
  • Zheng, Ke
  • Li, Wei
  • Hu, Xiaolei
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Activation
  • Derivatives
  • Chemical Reactions
  • Asymmetry
  • Nonlinearity
  • Catalysts
  • Maintenance
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, March 2010, Vol.16(12), pp.3736-3742
description: A direct catalytic asymmetric aldol-type reaction of 3-substituted-2-oxindoles with glyoxal derivatives and ethyl trifluoropyruvate, catalyzed by a chiral N,N'-dioxide-Sc(OTf) sub(3) (Tf=trifluoromethanesulfonyl) complex, has been developed that tolerates a wide range of substrates. The reaction proceeds in good yields and excellent enantioselectivities (up to 93% yield, 99:1 diastereomeric ratio (dr), and >99% enantiomeric excess (ee)) under mild conditions, to deliver 3-( alpha -hydroxy- beta -carbonyl) oxindoles with vicinal quaternary-tertiary or quaternary-quaternary stereocenters. Even with 1mol% catalyst loading or on scaleup (10mmol of starting material), maintenance of ee was observed, which showed the potential value of the catalyst system. In studies probing the reaction mechanism, a positive nonlinear effect was observed and Sc super(III)-based enolate intermediates were detected by using ESIMS. On the basis of the experimental results and previous...
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.200903471
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleCatalytic Asymmetric Synthesis of 3-( alpha -Hydroxy- beta -carbonyl) Oxindoles by a Sc super(III)-Catalyzed Direct Aldol-Type Reaction
creatorShen, Ke ; Liu, Xiaohua ; Zheng, Ke ; Li, Wei ; Hu, Xiaolei ; Lin, Lili ; Feng, Xiaoming
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subjectActivation ; Derivatives ; Chemical Reactions ; Asymmetry ; Nonlinearity ; Catalysts ; Maintenance ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA direct catalytic asymmetric aldol-type reaction of 3-substituted-2-oxindoles with glyoxal derivatives and ethyl trifluoropyruvate, catalyzed by a chiral N,N'-dioxide-Sc(OTf) sub(3) (Tf=trifluoromethanesulfonyl) complex, has been developed that tolerates a wide range of substrates. The reaction proceeds in good yields and excellent enantioselectivities (up to 93% yield, 99:1 diastereomeric ratio (dr), and >99% enantiomeric excess (ee)) under mild conditions, to deliver 3-( alpha -hydroxy- beta -carbonyl) oxindoles with vicinal quaternary-tertiary or quaternary-quaternary stereocenters. Even with 1mol% catalyst loading or on scaleup (10mmol of starting material), maintenance of ee was observed, which showed the potential value of the catalyst system. In studies probing the reaction mechanism, a positive nonlinear effect was observed and Sc super(III)-based enolate intermediates were detected by using ESIMS. On the basis of the experimental results and previous...
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titleCatalytic Asymmetric Synthesis of 3-( alpha -Hydroxy- beta -carbonyl) Oxindoles by a Sc super(III)-Catalyzed Direct Aldol-Type Reaction
descriptionA direct catalytic asymmetric aldol-type reaction of 3-substituted-2-oxindoles with glyoxal derivatives and ethyl trifluoropyruvate, catalyzed by a chiral N,N'-dioxide-Sc(OTf) sub(3) (Tf=trifluoromethanesulfonyl) complex, has been developed that tolerates a wide range of substrates. The reaction proceeds in good yields and excellent enantioselectivities (up to 93% yield, 99:1 diastereomeric ratio (dr), and >99% enantiomeric excess (ee)) under mild conditions, to deliver 3-( alpha -hydroxy- beta -carbonyl) oxindoles with vicinal quaternary-tertiary or quaternary-quaternary stereocenters. Even with 1mol% catalyst loading or on scaleup (10mmol of starting material), maintenance of ee was observed, which showed the potential value of the catalyst system. In studies probing the reaction mechanism, a positive nonlinear effect was observed and Sc super(III)-based enolate intermediates were detected by using ESIMS. On the basis of the experimental results and previous...
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titleCatalytic Asymmetric Synthesis of 3-( alpha -Hydroxy- beta -carbonyl) Oxindoles by a Sc super(III)-Catalyzed Direct Aldol-Type Reaction
authorShen, Ke ; Liu, Xiaohua ; Zheng, Ke ; Li, Wei ; Hu, Xiaolei ; Lin, Lili ; Feng, Xiaoming
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abstractA direct catalytic asymmetric aldol-type reaction of 3-substituted-2-oxindoles with glyoxal derivatives and ethyl trifluoropyruvate, catalyzed by a chiral N,N'-dioxide-Sc(OTf) sub(3) (Tf=trifluoromethanesulfonyl) complex, has been developed that tolerates a wide range of substrates. The reaction proceeds in good yields and excellent enantioselectivities (up to 93% yield, 99:1 diastereomeric ratio (dr), and >99% enantiomeric excess (ee)) under mild conditions, to deliver 3-( alpha -hydroxy- beta -carbonyl) oxindoles with vicinal quaternary-tertiary or quaternary-quaternary stereocenters. Even with 1mol% catalyst loading or on scaleup (10mmol of starting material), maintenance of ee was observed, which showed the potential value of the catalyst system. In studies probing the reaction mechanism, a positive nonlinear effect was observed and Sc super(III)-based enolate intermediates were detected by using ESIMS. On the basis of the experimental results and previous...
doi10.1002/chem.200903471
urlhttp://search.proquest.com/docview/1800498834/
date2010-03-22