Chiral 2-Aminobenzimidazole as Bifunctional Catalyst in the Asymmetric Electrophilic Amination of Unprotected 3-Substituted Oxindoles

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Título: Chiral 2-Aminobenzimidazole as Bifunctional Catalyst in the Asymmetric Electrophilic Amination of Unprotected 3-Substituted Oxindoles
Autor/es: Benavent, Llorenç | Baeza, Alejandro | Freckleton, Megan
Grupo/s de investigación o GITE: Nuevos Materiales y Catalizadores (MATCAT)
Centro, Departamento o Servicio: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Palabras clave: Organocatalysis | Electrophilic amination | Benzimidazoles | Asymmetric catalysis | Oxindoles
Área/s de conocimiento: Química Orgánica
Fecha de publicación: 6-jun-2018
Editor: MDPI
Cita bibliográfica: Benavent L, Baeza A, Freckleton M. Chiral 2-Aminobenzimidazole as Bifunctional Catalyst in the Asymmetric Electrophilic Amination of Unprotected 3-Substituted Oxindoles. Molecules. 2018; 23(6):1374. doi:10.3390/molecules23061374
Resumen: The use of readily available chiral trans-cyclohexanediamine-benzimidazole derivatives as bifunctional organocatalysts in the asymmetric electrophilic amination of unprotected 3-substituted oxindoles is presented. Different organocatalysts were evaluated; the most successful one contained a dimethylamino moiety (5). With this catalyst under optimized conditions, different oxindoles containing a wide variety of substituents at the 3-position were aminated in good yields and with good to excellent enantioselectivities using di-tert-butylazodicarboxylate as the aminating agent. The procedure proved to be also efficient for the amination of 3-substituted benzofuranones, although with moderate results. A bifunctional role of the catalyst, acting as Brønsted base and hydrogen bond donor, is proposed according to the experimental results observed.
Patrocinador/es: Financial support from the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P) and the University of Alicante (VIGROB-173, VIGROB-285, UAUSTI17-06, UADIF17-27) is acknowledged. M.F. thanks the University of Edinburgh for an ERASMUS fellowship.
URI: http://hdl.handle.net/10045/76549
ISSN: 1420-3049
DOI: 10.3390/molecules23061374
Idioma: eng
Tipo: info:eu-repo/semantics/article
Derechos: © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Revisión científica: si
Versión del editor: https://doi.org/10.3390/molecules23061374
Aparece en las colecciones:INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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