Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/155773
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Stereoselective synthesis of 1,3-diaminotruxillic acid derivatives: an advantageous combination of C-H-ortho-palladation and on-flow [2+2]-photocycloaddition in microreactors |
Autor: | Serrano, Elena CSIC; Juan, Alberto; García-Montero, Ángel; Soler, Tatiana; Jiménez-Márquez, Francisco; Cativiela, Carlos CSIC ORCID; Gómez, M. Victoria; Urriolabeitia, Esteban P. CSIC ORCID | Palabras clave: | C-H activation Photochemistry Palladium Microreactors Lactones |
Fecha de publicación: | 2016 | Editor: | Wiley-VCH | Citación: | Chemistry - A European Journal 22(1): 144-152 (2016) | Resumen: | The stereoselective synthesis of ε-isomers of dimethyl esters of 1,3-diaminotruxillic acid in three steps is reported. The first step is the ortho-palladation of (Z)-2-aryl-4-aryliden-5(4H)-oxazolones 1 to give dinuclear complexes 2 with bridging carboxylates. The reaction occurs through regioselective activation of the ortho-C-H bond of the 4-arylidene ring in carboxylic acids. The second step is the [2+2]-photocycloaddition of the C-C exocyclic bonds of the oxazolone skeleton in 2 to afford the corresponding dinuclear ortho-palladated cyclobutanes 3. This key step was performed very efficiently by using LED light sources with different wavelengths (465, 525 or 625 nm) in flow microreactors. The final step involved the depalladation of 3 by hydrogenation in methanol to afford the ε-1,3-diaminotruxillic acid derivatives as single isomers. | Versión del editor: | https://doi.org/10.1002/chem.201503742 | URI: | http://hdl.handle.net/10261/155773 | DOI: | 10.1002/chem.201503742 | Identificadores: | doi: 10.1002/chem.201503742 e-issn: 1521-3765 issn: 0947-6539 |
Aparece en las colecciones: | (ISQCH) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
---|---|---|---|---|
steromicro.pdf | 936,71 kB | Adobe PDF | Visualizar/Abrir |
CORE Recommender
PubMed Central
Citations
7
checked on 10-abr-2024
SCOPUSTM
Citations
26
checked on 19-abr-2024
WEB OF SCIENCETM
Citations
24
checked on 26-feb-2024
Page view(s)
348
checked on 24-abr-2024
Download(s)
572
checked on 24-abr-2024
Google ScholarTM
Check
Altmetric
Altmetric
Artículos relacionados:
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.