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Regio- and Enantioselective Aza-Diels-Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609

An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96% yield and 99% ee). Furthermore, the antimalarial compound NITD6... Full description

Journal Title: Angewandte Chemie (International Edition) 20150900, Vol.54(37), pp.10958-10962
Main Author: Zheng, Haifeng
Other Authors: Liu, Xiaohua , Xu, Chaoran , Xia, Yong , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201505717
Link: http://search.proquest.com/docview/1753515633/?pq-origsite=primo
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title: Regio- and Enantioselective Aza-Diels-Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609
format: Article
creator:
  • Zheng, Haifeng
  • Liu, Xiaohua
  • Xu, Chaoran
  • Xia, Yong
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Synthesis (Chemistry)
  • Derivatives
  • Pathways
  • Asymmetry
  • Imines
  • Heterocyclic Aromatic Compounds
  • Stereoselectivity
  • Ligands
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Angewandte Chemie (International Edition), 20150900, Vol.54(37), pp.10958-10962
description: An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96% yield and 99% ee). Furthermore, the antimalarial compound NITD609 could be obtained in three steps with an overall yield of 40.6%. Control experiments and operando IR experiments imply a concerted reaction pathway. The regioselectivity and exoselectivity result from pi - pi interactions between the two indoline rings of the two reactants. An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines leads to spiroindolone derivatives with high regio-, diastereo-, and enantioselectivity and also provides facile access to the valuable antimalarial drug NITD609. The stereoselectivity is thought to arise from pi - pi interactions between the two reactants and the chiral N,N'-dioxide ligand.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201505717
fulltext: fulltext
issn:
  • 14337851
  • 1433-7851
  • 15213773
  • 1521-3773
url: Link


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titleRegio- and Enantioselective Aza-Diels-Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609
creatorZheng, Haifeng ; Liu, Xiaohua ; Xu, Chaoran ; Xia, Yong ; Lin, Lili ; Feng, Xiaoming
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descriptionAn asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96% yield and 99% ee). Furthermore, the antimalarial compound NITD609 could be obtained in three steps with an overall yield of 40.6%. Control experiments and operando IR experiments imply a concerted reaction pathway. The regioselectivity and exoselectivity result from pi - pi interactions between the two indoline rings of the two reactants. An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines leads to spiroindolone derivatives with high regio-, diastereo-, and enantioselectivity and also provides facile access to the valuable antimalarial drug NITD609. The stereoselectivity is thought to arise from pi - pi interactions between the two reactants and the chiral N,N'-dioxide ligand.
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descriptionAn asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96% yield and 99% ee). Furthermore, the antimalarial compound NITD609 could be obtained in three steps with an overall yield of 40.6%. Control experiments and operando IR experiments imply a concerted reaction pathway. The regioselectivity and exoselectivity result from pi - pi interactions between the two indoline rings of the two reactants. An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines leads to spiroindolone derivatives with high regio-, diastereo-, and enantioselectivity and also provides facile access to the valuable antimalarial drug NITD609. The stereoselectivity is thought to arise from pi - pi interactions between the two reactants and the chiral N,N'-dioxide ligand.
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titleRegio- and Enantioselective Aza-Diels-Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609
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abstractAn asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96% yield and 99% ee). Furthermore, the antimalarial compound NITD609 could be obtained in three steps with an overall yield of 40.6%. Control experiments and operando IR experiments imply a concerted reaction pathway. The regioselectivity and exoselectivity result from pi - pi interactions between the two indoline rings of the two reactants. An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines leads to spiroindolone derivatives with high regio-, diastereo-, and enantioselectivity and also provides facile access to the valuable antimalarial drug NITD609. The stereoselectivity is thought to arise from pi - pi interactions between the two reactants and the chiral N,N'-dioxide ligand.
doi10.1002/anie.201505717
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date2015-09-07