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Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines

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Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines

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Vila, C.; Tortosa, A.; Blay, G.; Muñoz Roca, MDC.; Pedro, J. (2019). Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines. New Journal of Chemistry. 43(1):130-134. https://doi.org/10.1039/c8nj05577g

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Título: Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines
Autor: Vila, C. Tortosa, A. Blay, G. Muñoz Roca, María Del Carmen Pedro, J.R.
Entidad UPV: Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada
Fecha difusión:
Resumen:
[EN] An organocatalytic enantioselective functionalization in the carbocyclic ring of indoles with benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional organocatalyst. This aza-Friedel-Crafts ...[+]
Palabras clave: Friedel-Crafts reaction , Asymmetric-Synthesis , Alkylation , Ketimines , Hydroxyindoles , Construction , Derivatives , Inhibitors
Derechos de uso: Reserva de todos los derechos
Fuente:
New Journal of Chemistry. (issn: 1144-0546 )
DOI: 10.1039/c8nj05577g
Editorial:
The Royal Society of Chemistry
Versión del editor: https://doi.org/10.1039/c8nj05577g
Código del Proyecto:
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84900-P/ES/REACCIONES DE ADICION ENANTIOSELECTIVAS MEDIANTE SISTEMAS MULTICATALITICOS. HERRAMIENTAS PARA LA SINTESIS EFICIENTE DE MOLECULAS CON ACTIVIDAD FARMACOLOGICA/
info:eu-repo/grantAgreement/MINECO//RYC-2016-20187/
Agradecimientos:
Financial support from the Agencia Estatal de Investigación (AEI, Spanish Government) and Fondo Europeo de Desarrollo Regional (FEDER, European Union) (CTQ2017-84900-P) is acknowledged. C. V. thanks the Spanish Government ...[+]
Tipo: Artículo

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We only observed the product alkylated at the C-4 position and we did not observe in the crude 1 H NMR any other alkylated product

Cyclic ketimines such as 4-methylbenzo[ e ][1,2,3]oxathiazine 2,2-dioxide or 3-methylbenzo[ d ]isothiazole 1,1-dioxide were not reactive under the optimized reaction conditions

CCDC 1875758 ( 3e ) and CCDC 1846586 ( 7a ) contains the supplementary crystallographic data for this paper

De Munck, L., Monleón, A., Vila, C., & Pedro, J. R. (2017). Diarylprolinol as a Ligand for Enantioselective Alkynylation of Cyclic Imines. Advanced Synthesis & Catalysis, 359(9), 1582-1587. doi:10.1002/adsc.201601379

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