Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes
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Título: | Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes |
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Autor/es: | Calles, María | Puigcerver, Julio | Alonso, Diego A. | Alajarin, Mateo | Martinez-Cuezva, Alberto | Berna, Jose |
Grupo/s de investigación o GITE: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Prolinamide | Organocatalysts | Mechanical bond | [2]rotaxanes |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 11-mar-2020 |
Editor: | Royal Society of Chemistry |
Cita bibliográfica: | Chemical Science. 2020, 11: 3629-3635. doi:10.1039/d0sc00444h |
Resumen: | The synthesis of a pair of switchable interlocked prolinamides and their use as organocatalysts in three different enamine-activated processes are reported. A diacylaminopyridine moiety was incorporated into the thread for directing [2]rotaxane formation further allowing the association of complementary small molecules. The rotaxane-based systems were tested as organocatalysts in asymmetric enamine-mediated processes, revealing a significantly improved catalytic ability if compared with the non-interlocked thread. The presence of an electron-withdrawing nitro group at the macrocycle helps to achieve high conversions and enantioselectivities. These systems are able to interact with N-hexylthymine as a cofactor to form supramolecular catalysts displaying a divergent catalytic behaviour. The presence or absence of the cofactor controls the chemoselectivity in competitive reactions. |
Patrocinador/es: | This work was supported by the MINECO and MICINN (CTQ2017-87231-P, RYC-2017-22700 and PGC2018-096616-BI00) with joint financing by FEDER Funds and Fundación Seneca-CARM (Project 20811/PI/18). D. A. A. also thanks the University of Alicante for the financial support (VIGROB-173FI). |
URI: | http://hdl.handle.net/10045/105267 |
ISSN: | 2041-6520 (Print) | 2041-6539 (Online) |
DOI: | 10.1039/d0sc00444h |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1039/d0sc00444h |
Aparece en las colecciones: | INV - CESO - Artículos de Revistas |
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