Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as Organocatalysts
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Título: | Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as Organocatalysts |
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Autor/es: | Bañón Caballero, Abraham | Guillena, Gabriela | Nájera, Carmen |
Grupo/s de investigación o GITE: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Solvent-free | Enantioselective | Friedländer condensation | Wet 1,1′-binaphthalene-2,2′-diamine-derived prolinamides | Organocatalysis |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 10-may-2013 |
Editor: | American Chemical Society |
Cita bibliográfica: | Journal of Organic Chemistry. 2013, 78(11): 5349-5356. doi:10.1021/jo400522m |
Resumen: | Wet unsupported and supported 1,1′-binaphthalene-2,2′-diamine (BINAM) derived prolinamides are efficient organocatalysts under solvent-free conditions at room temperature to perform the synthesis of chiral tacrine analogues in good yields (up to 93%) and excellent enantioselectivies (up to 96%). The Friedländer reaction involved in this process takes place with several cyclohexanone derivatives and 2-aminoaromatic aldehydes, and it is compatible with the presence of either electron-withdrawing or electron-donating groups at the aromatic ring of the 2-aminoaryl aldehyde derivatives used as electrophiles. The reaction can be extended to cyclopentanone derivatives, affording a regioisomeric but separable mixture of products. The use of the wet silica gel supported organocatalyst, under solvent-free conditions, for this process led to the expected product (up to 87% enantiomeric excess), with its reuse being possible at least up to five times. |
Patrocinador/es: | This work was financially supported by the Ministerio de Ciencia e Innovación (MICINN: Projects: CTQ2010-20387 and Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (Prometeo/2009/039, the University of Alicante and the EU (ORCA action CM0905). A.B.-C. thanks the Spanish MICINN for a predoctoral fellowship (FPU AP2009-3601). |
URI: | http://hdl.handle.net/10045/38257 |
ISSN: | 0022-3263 (Print) | 1520-6904 (Online) |
DOI: | 10.1021/jo400522m |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2013 American Chemical Society |
Revisión científica: | si |
Versión del editor: | http://dx.doi.org/10.1021/jo400522m |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas INV - CESO - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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2013_Banon_etal_JOC_final.pdf | Versión final (acceso restringido) | 477,1 kB | Adobe PDF | Abrir Solicitar una copia |
2013_Banon_etal_JOC.pdf | Preprint (acceso abierto) | 294,86 kB | Adobe PDF | Abrir Vista previa |
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