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Título: | Ring-to-Thread Chirality Transfer in [2]Rotaxanes for the Synthesis of Enantioenriched Lactams |
Fecha de publicación: | 2-ago-2022 |
Fecha de defensa / creación: | 2022 |
Editorial: | Wiley-VCH |
Cita bibliográfica: | Angewandte Chemie International Edition, 61, 39, 2022, e202209904 |
ISSN: | Print: 1433-7851 Electronic: 1521-3773 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | Base-Promoted Cyclization Chirality Transfer Process Enantioselective Hydrogen-Bonded Rotaxanes Mechanostereoisomers |
Resumen: | The synthesis of chiral mechanically interlocked molecules has attracted a lot of attention in the last few years, with applications in different fields, such as asymmetric catalysis or sensing. Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, and nonsymmetric N-(arylmethyl)fumaramides as the axis. The base-promoted cyclization of the initial fumaramide thread allows enantioenriched value-added compounds, such as lactams of different ring sizes and amino acids, to be obtained. The chiral information is effectively transmitted across the mechanical bond from the encircling ring to the interlocked lactam. High levels of enantioselectivity and full control of the regioselectivity of the final cyclic compounds are attained. |
Autor/es principal/es: | Lopez-Leonardo, Carmen Saura Sanmartín, Adrián Marin-Luna, Marta Alajarín, Mateo Martinez-Cuezva, Alberto Berna, Jose |
Director/es: | Martinez-Cuezva, Alberto Berna, José |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
URI: | http://hdl.handle.net/10201/135763 |
DOI: | https://doi.org/10.1002/anie.202209904 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 10 |
Derechos: | info:eu-repo/semantics/openAccess Atribución 4.0 Internacional |
Descripción: | © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This manuscript version is made available under the CC-BY-NC 4.0 license https://creativecommons.org/licenses/by-nc/4.0/ This document is the Published Manuscript version of a Published Work that appeared in final form in Angewandte Chemie International Edition. To access the final edited and published work see https://doi.org/10.1002/anie.202209904 |
Aparece en las colecciones: | Artículos: Química Orgánica |
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Fichero | Descripción | Tamaño | Formato | |
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Ring-to-Thread Chirality Transfer in [2]Rotaxanes for the Synthesis of Enantioenriched Lactams.pdf | 6,98 MB | Adobe PDF | Visualizar/Abrir |
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