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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Montesinos Magraner, Marc; Vila Descals, Carlos; Rendón-Patiño, Alejandra; Blay Llinares, Gonzalo Perfil; Fernández Picot, Isabel; Muñoz, M. Carmen; Pedro, José Ramón
Aquest document és un/a article, creat/da en: 2016
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.

    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
distribuït sota llicència Creative Commons de Reconeixement-NoComercial 3.0 No adaptada

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