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Chiral N,N'-Dioxide-Organocatalyz ed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction

A highly regio-, diastereo- and enantioselective Michael addition-alkylation reaction between alpha -substituted cyano ketones and (Z)-bromonitrostyrenes has been realized by using a chiral N,N'-dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding... Full description

Journal Title: Chemistry: A European Journal October 2016, Vol.22(44), pp.15650-15653
Main Author: Feng, Juhua
Other Authors: Yuan, Xiao , Luo, Weiwei , Lin, Lili , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201603629
Link: http://search.proquest.com/docview/1855362912/?pq-origsite=primo
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title: Chiral N,N'-Dioxide-Organocatalyz ed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction
format: Article
creator:
  • Feng, Juhua
  • Yuan, Xiao
  • Luo, Weiwei
  • Lin, Lili
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Ketones
  • Derivatives
  • Asymmetry
  • Substrates
  • Catalysts
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, October 2016, Vol.22(44), pp.15650-15653
description: A highly regio-, diastereo- and enantioselective Michael addition-alkylation reaction between alpha -substituted cyano ketones and (Z)-bromonitrostyrenes has been realized by using a chiral N,N'-dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding multifunctionalized chiral 2,3-dihydrofurans were obtained in up to 95% yield with 95:5dr and 93% ee. Magic Mike: The catalytic asymmetric Michael addition/O-alkylation reaction of (Z)-bromonitrostyrenes with alpha -substituted cyano ketones is accomplished by using an efficient N,N'-dioxide organocatalyst. A range of 2,3-dihydrofuran derivatives is obtained with high to excellent enantiomeric excesses and excellent diastereomeric ratios.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201603629
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleChiral N,N'-Dioxide-Organocatalyz ed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction
creatorFeng, Juhua ; Yuan, Xiao ; Luo, Weiwei ; Lin, Lili ; Liu, Xiaohua ; Feng, Xiaoming
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subjectKetones ; Derivatives ; Asymmetry ; Substrates ; Catalysts ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA highly regio-, diastereo- and enantioselective Michael addition-alkylation reaction between alpha -substituted cyano ketones and (Z)-bromonitrostyrenes has been realized by using a chiral N,N'-dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding multifunctionalized chiral 2,3-dihydrofurans were obtained in up to 95% yield with 95:5dr and 93% ee. Magic Mike: The catalytic asymmetric Michael addition/O-alkylation reaction of (Z)-bromonitrostyrenes with alpha -substituted cyano ketones is accomplished by using an efficient N,N'-dioxide organocatalyst. A range of 2,3-dihydrofuran derivatives is obtained with high to excellent enantiomeric excesses and excellent diastereomeric ratios.
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descriptionA highly regio-, diastereo- and enantioselective Michael addition-alkylation reaction between alpha -substituted cyano ketones and (Z)-bromonitrostyrenes has been realized by using a chiral N,N'-dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding multifunctionalized chiral 2,3-dihydrofurans were obtained in up to 95% yield with 95:5dr and 93% ee. Magic Mike: The catalytic asymmetric Michael addition/O-alkylation reaction of (Z)-bromonitrostyrenes with alpha -substituted cyano ketones is accomplished by using an efficient N,N'-dioxide organocatalyst. A range of 2,3-dihydrofuran derivatives is obtained with high to excellent enantiomeric excesses and excellent diastereomeric ratios.
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abstractA highly regio-, diastereo- and enantioselective Michael addition-alkylation reaction between alpha -substituted cyano ketones and (Z)-bromonitrostyrenes has been realized by using a chiral N,N'-dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding multifunctionalized chiral 2,3-dihydrofurans were obtained in up to 95% yield with 95:5dr and 93% ee. Magic Mike: The catalytic asymmetric Michael addition/O-alkylation reaction of (Z)-bromonitrostyrenes with alpha -substituted cyano ketones is accomplished by using an efficient N,N'-dioxide organocatalyst. A range of 2,3-dihydrofuran derivatives is obtained with high to excellent enantiomeric excesses and excellent diastereomeric ratios.
doi10.1002/chem.201603629
urlhttp://search.proquest.com/docview/1855362912/
date2016-10-24