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Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Alkylidene Malonates

We demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide-Ni super(II) complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of trans-pyraz... Full description

Journal Title: Chemistry: A European Journal April 2013, Vol.19(16), pp.5134-5140
Main Author: Li, Jiangting
Other Authors: Lian, Xiangjin , 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.201203891
Link: http://search.proquest.com/docview/1778029270/?pq-origsite=primo
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title: Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Alkylidene Malonates
format: Article
creator:
  • Li, Jiangting
  • Lian, Xiangjin
  • Liu, Xiaohua
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Cycloaddition
  • Alkylidene
  • Derivatives
  • Asymmetry
  • Imines
  • Catalysts
  • Esters
  • Isomers
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
  • Asymmetric Catalysis
  • Azomethine Imines
  • Cycloaddition
  • N,N'-Dioxide Ligands
  • Nickel
ispartof: Chemistry: A European Journal, April 2013, Vol.19(16), pp.5134-5140
description: We demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide-Ni super(II) complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of trans-pyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97%ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed. Pyrazolone products: The asymmetric [3+2] dipolar cycloaddition...
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201203891
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleNickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Alkylidene Malonates
creatorLi, Jiangting ; Lian, Xiangjin ; Liu, Xiaohua ; Lin, Lili ; Feng, Xiaoming
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subjectCycloaddition ; Alkylidene ; Derivatives ; Asymmetry ; Imines ; Catalysts ; Esters ; Isomers ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC) ; Asymmetric Catalysis ; Azomethine Imines ; Cycloaddition ; N,N'-Dioxide Ligands ; Nickel
descriptionWe demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide-Ni super(II) complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of trans-pyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97%ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed. Pyrazolone products: The asymmetric [3+2] dipolar cycloaddition...
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titleNickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Alkylidene Malonates
descriptionWe demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide-Ni super(II) complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of trans-pyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97%ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed. Pyrazolone products: The asymmetric [3+2] dipolar cycloaddition...
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titleNickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Alkylidene Malonates
authorLi, Jiangting ; Lian, Xiangjin ; Liu, Xiaohua ; Lin, Lili ; Feng, Xiaoming
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abstractWe demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide-Ni super(II) complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of trans-pyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97%ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed. Pyrazolone products: The asymmetric [3+2] dipolar cycloaddition...
doi10.1002/chem.201203891
urlhttp://search.proquest.com/docview/1778029270/
date2013-04-15