Montesinos Magraner, M.; Vila, C.; Rendón Patiño, A.; Blay, G.; Fernández, I.; Muñoz Roca, MDC.; Pedro, JR. (2016). Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring. ACS Catalysis. 6(4):2689-2693. https://doi.org/10.1021/acscatal.6b00260
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/72278
Title:
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Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
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Author:
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Montesinos Magraner, Marc
Vila, Carlos
Rendón Patiño, Alejandra
Blay, Gonzalo
Fernández, Isabel
Muñoz Roca, María del Carmen
Pedro, José R.
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UPV Unit:
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Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería del Diseño - Escola Tècnica Superior d'Enginyeria del Disseny
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Issued date:
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Abstract:
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The first general catalytic method for the, so far elusive, enantioselective Friedel−Crafts functionalization of
indoles in the carbocyclic ring is presented. This transformation contrasts with the usual tendency of these ...[+]
The first general catalytic method for the, so far elusive, enantioselective Friedel−Crafts functionalization of
indoles in the carbocyclic ring is presented. This transformation contrasts with the usual tendency of these heterocycles to react
at the azole ring. For this purpose, the four regioisomeric hydroxy carbocyclic-substituted indoles were reacted with several isatinderived
ketimines, using a Cinchona alkaloid-based squaramide, in a low 0.5−5 mol % catalyst loading, as a bifunctional catalyst.
This methodology allows the functionalization of indoles in every position of the carbocyclic ring in a regio- and enantioselective
fashion, by switching only the position of the hydroxy group in the starting material. Furthermore, several transformations were
carried out, including the reductive elimination of the hydroxy group.
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Subjects:
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Asymmetric catalysis
,
Organocatalysis
,
Friedel−Crafts reaction
,
Indoles
,
Phenols
,
Isatin-derived ketimines
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Copyrigths:
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Reserva de todos los derechos
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Source:
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ACS Catalysis. (issn:
2155-5435
) (eissn:
2155-5435
)
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DOI:
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10.1021/acscatal.6b00260
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Publisher:
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American Chemical Society
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Publisher version:
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http://dx.doi.org/10.1021/acscatal.6b00260
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Project ID:
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info:eu-repo/grantAgreement/MINECO//CTQ2013-47494-P/ES/NUEVOS RETOS EN EL DESARROLLO DE PROCESOS ENANTIOSELECTIVOS DE FORMACION DE ENLACES C-C MEDIANTE CATALISIS DUAL COOPERATIVA./
info:eu-repo/grantAgreement/GVA//ISIC2012%2F001/
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Thanks:
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Financial support from MINECO (Gobierno de Espana; CTQ2013-47494-P) and from Generalitat Valenciana (ISIC2012/001) is gratefully acknowledged. M.M-M. thanks Universitat de Valencia for a predoctoral grant, and C.V. thanks ...[+]
Financial support from MINECO (Gobierno de Espana; CTQ2013-47494-P) and from Generalitat Valenciana (ISIC2012/001) is gratefully acknowledged. M.M-M. thanks Universitat de Valencia for a predoctoral grant, and C.V. thanks MINECO for a JdC contract. Access to NMR, X-ray, and MS facilities from SCSIE-UV is also acknowledged.
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Type:
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Artículo
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