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10.1021/jacs.6b05581
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Título: | Stereocontrolled synthesis of -lactams within [2]rotaxanes: a showcase of the chemical consequences of the mechanical bonding |
Fecha de publicación: | 29-jun-2016 |
Editorial: | ACS |
Cita bibliográfica: | J. Am. Chem. Soc. 2016, 138, 28, 8726–8729 |
ISSN: | 0002-7863 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | rotaxane cyclization lactam macrocycle activation |
Resumen: | The intramolecular cyclization of N-benzyl fumaramide [2]rotaxanes is described. The mechanical bond of these substrates activates this transformation to proceed in high yields and in a regio- and diastereoselective manner giving interlocked 3,4-disubstituted trans azetidin-2-ones. This activation effect differs from the common shielding stabilization of threaded functions through amide-based macrocycles promoting an unusual and disfavored 4-exo-trig ring closure. Further kinetic and synthetic studies allowed us to produce an original approach towards -lactams through a one-pot protocol based on an intramolecular ring closure followed by a thermally-induced dethreading step. The advantages for carrying out this cyclization in the confined space of a benzylic amide macrocycle were attributed to the anchimeric assistance of the surrounding macrocycle. |
Autor/es principal/es: | Martinez-Cuezva, Alberto Lopez-Leonardo, Carmen Bautista, Delia Alajarín, Mateo Berná Cánovas, José |
Versión del editor: | https://pubs.acs.org/doi/10.1021/jacs.6b05581 |
URI: | http://hdl.handle.net/10201/113634 |
DOI: | 10.1021/jacs.6b05581 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 6 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Aparece en las colecciones: | Artículos: Química Orgánica |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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Lactams OA.pdf | 803,78 kB | Adobe PDF | Visualizar/Abrir |
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