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10.1039/C8QO00255J
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Título: | Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3+2] annulations of ketenimines with donor-acceptor oxiranes and aziridines |
Fecha de publicación: | 9-may-2018 |
Fecha de defensa / creación: | 2018 |
Editorial: | Royal Society of Chemistry |
Cita bibliográfica: | Org. Chem. Front., 2018, 5, 2020-2029. |
ISSN: | 2052-4129 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | CYCLOADDITIONS STEREOSELECTIVITY CATALYZED ANNULATION AZOMETHINE YLIDES DFT CALCULATIONS |
Resumen: | Efficient [3 + 2] annulations of N-aryl-C,C-diphenyl ketenimines with metallo-carbonyl and metallo-azomethine ylides, generated via the respective Yb(OTf)3 and Y(OTf)3 promoted carbon–carbon bond heterolysis of donor–acceptor oxiranes and aziridines, have been accomplished. These reactions proceeded under mild conditions and supplied a general methodology for the regioselective construction of structurally complex oxazolidines and pyrrolidines. Moreover, heating neat mixtures of N-aryl-C,C-diphenyl ketenimines and diethyl aziridine-2,3-dicarboxylates led to imidazolidine derivatives. A computational study concluded in stepwise mechanisms for these [3 + 2] annulations, also shedding light on their regioselectivity, concerning which of the two cumulated double bonds of the ketenimine becomes involved in the reaction with the ylide. |
Autor/es principal/es: | Alajarín, Mateo Banon, David Egea, Adrian Marin-Luna, Marta Orenes, Raul A. Vidal, Angel |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://pubs.rsc.org/en/content/articlelanding/2018/qo/c8qo00255j |
URI: | http://hdl.handle.net/10201/102602 |
DOI: | 10.1039/C8QO00255J |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 11 |
Derechos: | info:eu-repo/semantics/openAccess Atribución-NoComercial-SinDerivadas 3.0 España |
Aparece en las colecciones: | Artículos: Química Orgánica |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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2018OCF_AV_Annulations of ketenimines.pdf | 944,97 kB | Adobe PDF | Visualizar/Abrir |
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