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Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines and pyrrolines. These reactions are highly stereo- and regioselective, and have the potential to form four new contiguous stereocenters. Azomethine ylides thus have high utility in total synthesis, and formation of chiral ligands and pharmaceuticals. Azomethine ylides can be generated from many sources, including aziridines, imines, and iminiums. They are often generated in situ, and immediately reacted with dipolarophiles.

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rdfs:label
  • Azomethin-Ylide (de)
  • Azomethine ylide (en)
  • Iluros de azometina (es)
rdfs:comment
  • Azomethin-Ylide sind stickstoffhaltige 1,3-Dipole, welche aus einem Iminium und einem Carbanion bestehen. Sie werden in 1,3-dipolaren Cycloadditionen verwendet. So können Heterocyclen, wie Pyrrolidine oder Pyrroline aufgebaut werden. Diese Reaktionen sind hoch stereo- und regioselektiv und besitzen das Potential vier zusammenhängende Stereozentren zu generieren. Azomethin-Ylide haben dadurch großen Nutzen in der Totalsynthese sowie der Herstellung von chiralen Liganden und Medikamenten. Azomethin-Ylide können aus verschiedenen Verbindungen, wie Aziridinen, Iminen und Iminium-Ionen hergestellt werden. Meist erfolgt die Herstellung in situ mit anschließender Reaktion mit einem Dipolarophil. (de)
  • Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines and pyrrolines. These reactions are highly stereo- and regioselective, and have the potential to form four new contiguous stereocenters. Azomethine ylides thus have high utility in total synthesis, and formation of chiral ligands and pharmaceuticals. Azomethine ylides can be generated from many sources, including aziridines, imines, and iminiums. They are often generated in situ, and immediately reacted with dipolarophiles. (en)
  • Los iluros de azometina son 1,3-dipolos a base de nitrógeno, que consta de un ion de iminio junto a un carbanión. Se utilizan en reacciones de cicloadición 1,3-dipolar para formar heterociclos de 5 miembros, incluyendo pirrolidinas y pirrolinas.​​​ Estas reacciones son altamente estereo- y regioselectivas, y tienen el potencial para formar cuatro nuevos estereocentros contiguos. Por lo tanto, los iluros de azometina tienen gran utilidad en síntesis y formación de ligandos quirales y productos farmacéuticos. Los iluros de azometina pueden ser generados a partir de muchas fuentes, incluyendo aziridinas, iminas, y iminios. A menudo se generan in situ, e inmediatamente se hacen reaccionar con dipolarófilos. (es)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_2.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Aziridine_opening.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_cycloaddition.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_cycloaddition_rxn.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_from_condensation.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_from_imine.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_from_munchnone.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_resonance.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Azomethine_ylide_shapes.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Benzodiazepinones_from_azomethine_ylides.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Deprotonation_of_iminium.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Synthesis_of_Martinellic_acid.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Ylide_1,7_electrocyclization.png
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