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Asymmetric Hetero-Diels-Alder Reaction of Danishefsky's Diene with alpha -Ketoesters and Isatins Catalyzed by a Chiral N,N'-Dioxide/Magnesium(II) Complex

A highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins has been realized by using a chiral N,N'-dioxide/Mg super(II) complex. In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasub... Full description

Journal Title: Chemistry: A European Journal October 2014, Vol.20(44), pp.14493-14498
Main Author: Zheng, Jianfeng
Other Authors: Lin, Lili , Fu, Kai , Zhang, Yulong , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201404144
Link: http://search.proquest.com/docview/1786196360/?pq-origsite=primo
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title: Asymmetric Hetero-Diels-Alder Reaction of Danishefsky's Diene with alpha -Ketoesters and Isatins Catalyzed by a Chiral N,N'-Dioxide/Magnesium(II) Complex
format: Article
creator:
  • Zheng, Jianfeng
  • Lin, Lili
  • Fu, Kai
  • Zhang, Yulong
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Dienes
  • Chemical Reactions
  • Asymmetry
  • Catalysts
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, October 2014, Vol.20(44), pp.14493-14498
description: A highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins has been realized by using a chiral N,N'-dioxide/Mg super(II) complex. In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3-dihydropyran-4-ones in up to 99% yield and more than 99%ee in two hours. Highly asymmetric: A highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins catalyzed by a chiral Mg super(II)/N,N'-dioxide complex has been developed (see scheme; TMS=trimethylsilyl). In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3-dihydropyran-4-ones in up to 99% yield and more than 99%ee in two hours.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201404144
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleAsymmetric Hetero-Diels-Alder Reaction of Danishefsky's Diene with alpha -Ketoesters and Isatins Catalyzed by a Chiral N,N'-Dioxide/Magnesium(II) Complex
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descriptionA highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins has been realized by using a chiral N,N'-dioxide/Mg super(II) complex. In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3-dihydropyran-4-ones in up to 99% yield and more than 99%ee in two hours. Highly asymmetric: A highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins catalyzed by a chiral Mg super(II)/N,N'-dioxide complex has been developed (see scheme; TMS=trimethylsilyl). In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3-dihydropyran-4-ones in up to 99% yield and more than 99%ee in two hours.
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titleAsymmetric Hetero-Diels-Alder Reaction of Danishefsky's Diene with alpha -Ketoesters and Isatins Catalyzed by a Chiral N,N'-Dioxide/Magnesium(II) Complex
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abstractA highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins has been realized by using a chiral N,N'-dioxide/Mg super(II) complex. In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3-dihydropyran-4-ones in up to 99% yield and more than 99%ee in two hours. Highly asymmetric: A highly enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with alpha -ketoesters and isatins catalyzed by a chiral Mg super(II)/N,N'-dioxide complex has been developed (see scheme; TMS=trimethylsilyl). In the presence of only 0.1-0.5mol% catalyst, a series of substrates were transformed into the corresponding tetrasubstituted 2,3-dihydropyran-4-ones in up to 99% yield and more than 99%ee in two hours.
doi10.1002/chem.201404144
urlhttp://search.proquest.com/docview/1786196360/
date2014-10-27