Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
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Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring

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Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring

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dc.contributor.author Montesinos Magraner, Marc
dc.contributor.author Vila Descals, Carlos
dc.contributor.author Rendón-Patiño, Alejandra
dc.contributor.author Blay Llinares, Gonzalo
dc.contributor.author Fernández Picot, Isabel
dc.contributor.author Muñoz, M. Carmen
dc.contributor.author Pedro, José Ramón
dc.date.accessioned 2016-06-14T08:02:42Z
dc.date.available 2016-06-14T08:02:42Z
dc.date.issued 2016
dc.identifier.uri http://hdl.handle.net/10550/54053
dc.description.abstract 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.
dc.language.iso eng
dc.relation.ispartof Acs Catalysis, 2016, vol. 6, p. 2689-2693
dc.rights.uri info:eu-repo/semantics/openAccess
dc.source Montesinos Magraner, Marc Vila Descals, Carlos Rendón-Patiño, Alejandra Blay Llinares, Gonzalo Fernández Picot, Isabel Muñoz, M. Carmen Pedro Llinares, José Ramón 2016 Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring Acs Catalysis 6 2689 2693
dc.subject Química
dc.title Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
dc.type info:eu-repo/semantics/article
dc.date.updated 2016-06-14T08:02:43Z
dc.identifier.doi 10.1021/acscatal.6b00260
dc.identifier.idgrec 110092

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