Chiral 2-Aminobenzimidazole as Bifunctional Catalyst in the Asymmetric Electrophilic Amination of Unprotected 3-Substituted Oxindoles
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Campo DC | Valor | Idioma |
---|---|---|
dc.contributor | Nuevos Materiales y Catalizadores (MATCAT) | es_ES |
dc.contributor.author | Benavent, Llorenç | - |
dc.contributor.author | Baeza, Alejandro | - |
dc.contributor.author | Freckleton, Megan | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es_ES |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es_ES |
dc.date.accessioned | 2018-06-14T08:03:58Z | - |
dc.date.available | 2018-06-14T08:03:58Z | - |
dc.date.issued | 2018-06-06 | - |
dc.identifier.citation | 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 | es_ES |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/10045/76549 | - |
dc.description.abstract | 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. | es_ES |
dc.description.sponsorship | 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. | es_ES |
dc.language | eng | es_ES |
dc.publisher | MDPI | es_ES |
dc.rights | © 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/). | es_ES |
dc.subject | Organocatalysis | es_ES |
dc.subject | Electrophilic amination | es_ES |
dc.subject | Benzimidazoles | es_ES |
dc.subject | Asymmetric catalysis | es_ES |
dc.subject | Oxindoles | es_ES |
dc.subject.other | Química Orgánica | es_ES |
dc.title | Chiral 2-Aminobenzimidazole as Bifunctional Catalyst in the Asymmetric Electrophilic Amination of Unprotected 3-Substituted Oxindoles | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.peerreviewed | si | es_ES |
dc.identifier.doi | 10.3390/molecules23061374 | - |
dc.relation.publisherversion | https://doi.org/10.3390/molecules23061374 | es_ES |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/MINECO//CTQ2015-66624-P | - |
Aparece en las colecciones: | INV - MATCAT - Artículos de Revistas INV - AMIC - Artículos de Revistas |
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