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10.1055/s-0037-1611705
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Título: | Stereocontrol in the Synthesis of β-Lactams Arising from the Interlocked Structure of Benzylfumaramide-Based Hydrogen-Bonded [2]Rotaxanes |
Fecha de publicación: | 18-ene-2019 |
Fecha de defensa / creación: | 2019 |
Editorial: | Thieme |
Cita bibliográfica: | Synlett 2019, 30, 893–902. |
ISSN: | 0936-5214 1437-2096 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | mechanical bonding cyclization stereoselectivity beta-lactams macrocycles |
Resumen: | β-Lactams are highly valuable compounds due to their antibiotic activity. Among the number of well-established methodologies for building this privileged scaffold, our research group has settled on a novel synthetic approach for their preparation. This Account focuses on our latest progress in the synthesis of these compounds through a novel base-promoted intramolecular cyclization of benzylfumaramide-based rotaxanes. The mechanical bond plays a significant role in the process by activating the cyclization inside the macrocycle void, avoiding the formation of byproducts and fully controlling the diastereoselectivity. Further investigations on this transformation led to the formation of enantioenriched 2-azetidinones. The cyclization of enantiopure interlocked α-methylbenzylfumaramides allows the formation of two new stereogenic centers in the lactamic four-membered ring, one of them a quaternary carbon, keeping the initial configuration of the chiral group of the starting material. |
Autor/es principal/es: | Martinez-Cuezva, Alberto Lopez-Leonardo, Carmen Alajarín, Mateo Berná Cánovas, José |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://www.thieme-connect.com/products/ejournals/html/10.1055/s-0037-1611705 |
URI: | http://hdl.handle.net/10201/102481 |
DOI: | 10.1055/s-0037-1611705 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 10 |
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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20Synlett_Account Interlocked Lactams_AV.pdf | 1,83 MB | Adobe PDF | Visualizar/Abrir |
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