Binap-gold(I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1,3-dipolar cycloaddition of azomethine ylides
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Título: | Binap-gold(I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1,3-dipolar cycloaddition of azomethine ylides |
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Autor/es: | Martín Rodríguez, María | Nájera, Carmen | Sansano, Jose M. | Wu, Feng-Liu |
Grupo/s de investigación o GITE: | Procesos Catalíticos en Síntesis Orgánica |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica |
Palabras clave: | Catalyst | Prolines |
Área/s de conocimiento: | Química Orgánica |
Fecha de creación: | 2010 |
Fecha de publicación: | 30-jun-2010 |
Editor: | Elsevier |
Cita bibliográfica: | MARTÍN RODRÍGUEZ, María, et al. "Binap-gold(I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1,3-dipolar cycloaddition of azomethine ylides". Tetrahedron: Asymmetry. Vol. 21, No. 9-10 (17 May 2010). ISSN 0957-4166, pp. 1184-1186 |
Resumen: | Highly enantioselective 1,3-dipolar cycloadditions of amino acid-derived azomethine ylides with alkenes have been performed, for the first time, under gold-catalysis using (Sa)- or (Ra)-Binap-gold(I) trifluoroacetate complexes, with the cationic Binap-gold acting as a Lewis acid and the counteranion as a base. Maleimides and trans-1,2-bis(phenylsulfonyl)ethylene were reacted with imino esters at room temperature in the absence of a base to afford, in very good yields, the corresponding polysubstituted prolines with total endo-diastereoselection and higher enantioselectivities than the Binap-silver trifluoroacetate complex. |
Patrocinador/es: | This work has been supported by the DGES of the Spanish Ministerio de Educación y Ciencia (MEC) (Consolider INGENIO 2010 CSD2007-00006, and CTQ2007-62771/BQU), by the Generalitat Valenciana (PROMETEO/2009/039), and by the University of Alicante. M.M.-R. thanks MEC for a predoctoral fellowship and F.-L. W. thanks the UQ Graduate School for a Research Travel Grant. |
URI: | http://hdl.handle.net/10045/14318 |
ISSN: | 0957-4166 (Print) | 1362-511X (Online) |
DOI: | 10.1016/j.tetasy.2010.06.011 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Revisión científica: | si |
Versión del editor: | http://dx.doi.org/10.1016/j.tetasy.2010.06.011 |
Aparece en las colecciones: | INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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TETASY58069-1.pdf | Versión final (acceso restringido) | 508,14 kB | Adobe PDF | Abrir Solicitar una copia |
TetrahedronAssymmV1.doc | Preprint (acceso libre) | 1,16 MB | Microsoft Word | Abrir Vista previa |
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