Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/154852
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Azomethine ylides from nitrones: Using catalytic nBuLi for the totally stereoselective synthesis of trans-2-alkyl-3-oxazolines |
Autor: | Juste-Navarro, Verónica CSIC ORCID; Delso, J. Ignacio CSIC ORCID; Tejero, Tomás CSIC ORCID; Merino, Pedro CSIC ORCID | Palabras clave: | Density functional calculations lithium Oxazolines Nitrones Azomethine ylides |
Fecha de publicación: | 2016 | Editor: | Wiley-VCH | Citación: | Chemistry - A European Journal 22(33): 11527-11532 (2016) | Resumen: | The cycloaddition of azomethine ylide N-oxides (nitrone ylides) with aldehydes provides 3-oxazolines in a completely stereoselective manner in the presence of a catalytic amount of n-butyllithium. The process involves an initial nucleophilic attack on the aldehyde, followed by intramolecular oxygen addition to the nitrone moiety and lithium-assisted elimination of water, regenerating the catalytic species. Various Li-based catalytic systems are possible and the in situ generated water is required for continuing the catalytic cycle. The best results are observed with 20 mol % of n-butyllithium, whereas the use of stoichiometric amounts inhibit the rate of catalysis. Experimental, spectroscopic, and computational mechanistic studies have provided evidence of lithium-ion catalysis and rationalized several competing catalytic pathways. | URI: | http://hdl.handle.net/10261/154852 | DOI: | 10.1002/chem.201602159 | Identificadores: | doi: 10.1002/chem.201602159 e-issn: 1521-3765 issn: 0947-6539 |
Aparece en las colecciones: | (ISQCH) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
---|---|---|---|---|
accesoRestringido.pdf | 15,38 kB | Adobe PDF | Visualizar/Abrir |
CORE Recommender
SCOPUSTM
Citations
20
checked on 08-mar-2024
WEB OF SCIENCETM
Citations
17
checked on 28-feb-2024
Page view(s)
272
checked on 18-mar-2024
Download(s)
97
checked on 18-mar-2024
Google ScholarTM
Check
Altmetric
Altmetric
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.