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Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric alpha -Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex

A highly enantioselective alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselec... Full description

Journal Title: Chemistry: A European Journal June 2010, Vol.16(22), pp.6632-6637
Main Author: Yang, Zhigang
Other Authors: Wang, Zhen , Bai, Sha , Shen, Ke , Chen, Donghui , 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.201000126
Link: http://search.proquest.com/docview/1800489197/?pq-origsite=primo
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title: Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric alpha -Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
format: Article
creator:
  • Yang, Zhigang
  • Wang, Zhen
  • Bai, Sha
  • Shen, Ke
  • Chen, Donghui
  • Liu, Xiaohua
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Molecular Sieves
  • Derivatives
  • Asymmetry
  • Substrates
  • Catalysts
  • Optical Activity
  • Catalysis
  • Animated
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, June 2010, Vol.16(22), pp.6632-6637
description: A highly enantioselective alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5mol% of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center. Animated amination: An alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex has been developed to afford the corresponding...
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201000126
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleHighly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric alpha -Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
creatorYang, Zhigang ; Wang, Zhen ; Bai, Sha ; Shen, Ke ; Chen, Donghui ; Liu, Xiaohua ; Lin, Lili ; Feng, Xiaoming
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subjectMolecular Sieves ; Derivatives ; Asymmetry ; Substrates ; Catalysts ; Optical Activity ; Catalysis ; Animated ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA highly enantioselective alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5mol% of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center. Animated amination: An alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex has been developed to afford the corresponding...
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titleHighly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric alpha -Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
descriptionA highly enantioselective alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5mol% of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center. Animated amination: An alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex has been developed to afford the corresponding...
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titleHighly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric alpha -Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
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abstractA highly enantioselective alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5mol% of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center. Animated amination: An alpha -amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf) sub(3)/N,N'-dioxide complex has been developed to afford the corresponding...
doi10.1002/chem.201000126
urlhttp://search.proquest.com/docview/1800489197/
date2010-06-11