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Catalytic Michael/Ring-Closure Reaction of [alpha],[beta]-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (-)-Paroxetine

A highly enantioselective tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with hi... Full description

Journal Title: Chemistry: A European Journal October 2016, Vol.22(42), pp.15119-15124
Main Author: Zhang, Yu
Other Authors: Liao, Yuting , Liu, Xiaohua , Yao, Qian , Zhou, Yuhang , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201603056
Link: http://search.proquest.com/docview/1845815785/?pq-origsite=primo
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title: Catalytic Michael/Ring-Closure Reaction of [alpha],[beta]-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (-)-Paroxetine
format: Article
creator:
  • Zhang, Yu
  • Liao, Yuting
  • Liu, Xiaohua
  • Yao, Qian
  • Zhou, Yuhang
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Sieves
  • Cascade Chemical Reactions
  • Asymmetry
  • Origins
  • Nonlinearity
  • Synthesis
  • Methodology
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, October 2016, Vol.22(42), pp.15119-15124
description: A highly enantioselective tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with high yields and diastereo- and enantioselectivities. Moreover, this methodology could be used for gram-scale manipulation and was successfully applied to the synthesis of (-)-paroxetine. Further nonlinear and HRMS studies revealed that the real catalytically active species was a monomeric L-PMe sub(2)-Yb super(3+) complex. A plausible transition state was proposed to explain the origin of the asymmetric induction. Tandem heterocycle formation: A tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex to give the chiral glutarimides with high yields and diastereo- and enantioselectivities (see scheme: Tf=trifluoromethanesulfonyl; M.S.=molecular sieves). The methodology was successfully applied to the synthesis of (-)-paroxetine.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201603056
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleCatalytic Michael/Ring-Closure Reaction of [alpha],[beta]-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (-)-Paroxetine
creatorZhang, Yu ; Liao, Yuting ; Liu, Xiaohua ; Yao, Qian ; Zhou, Yuhang ; Lin, Lili ; Feng, Xiaoming
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ispartofChemistry: A European Journal, October 2016, Vol.22(42), pp.15119-15124
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subjectSieves ; Cascade Chemical Reactions ; Asymmetry ; Origins ; Nonlinearity ; Synthesis ; Methodology ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA highly enantioselective tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with high yields and diastereo- and enantioselectivities. Moreover, this methodology could be used for gram-scale manipulation and was successfully applied to the synthesis of (-)-paroxetine. Further nonlinear and HRMS studies revealed that the real catalytically active species was a monomeric L-PMe sub(2)-Yb super(3+) complex. A plausible transition state was proposed to explain the origin of the asymmetric induction. Tandem heterocycle formation: A tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex to give the chiral glutarimides with high yields and diastereo- and enantioselectivities (see scheme: Tf=trifluoromethanesulfonyl; M.S.=molecular sieves). The methodology was successfully applied to the synthesis of (-)-paroxetine.
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titleCatalytic Michael/Ring-Closure Reaction of [alpha],[beta]-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (-)-Paroxetine
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titleCatalytic Michael/Ring-Closure Reaction of [alpha],[beta]-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (-)-Paroxetine
authorZhang, Yu ; Liao, Yuting ; Liu, Xiaohua ; Yao, Qian ; Zhou, Yuhang ; Lin, Lili ; Feng, Xiaoming
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abstractA highly enantioselective tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with high yields and diastereo- and enantioselectivities. Moreover, this methodology could be used for gram-scale manipulation and was successfully applied to the synthesis of (-)-paroxetine. Further nonlinear and HRMS studies revealed that the real catalytically active species was a monomeric L-PMe sub(2)-Yb super(3+) complex. A plausible transition state was proposed to explain the origin of the asymmetric induction. Tandem heterocycle formation: A tandem Michael/ring-closure reaction of [alpha],[beta]-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N'-dioxide-Yb(OTf ) sub(3) complex to give the chiral glutarimides with high yields and diastereo- and enantioselectivities (see scheme: Tf=trifluoromethanesulfonyl; M.S.=molecular sieves). The methodology was successfully applied to the synthesis of (-)-paroxetine.
doi10.1002/chem.201603056
urlhttp://search.proquest.com/docview/1845815785/
date2016-10-10