Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines
NAGIOS: RODERIC FUNCIONANDO

Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines

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Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines

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Vila Descals, Carlos; Rendón-Patiño, Alejandra; Montesinos Magraner, Marc; Blay Llinares, Gonzalo Perfil; Muñoz, M. Carmen; Pedro, José Ramón
This document is a artículoDate2018
A highly enantioselective addition o hydroxyquinolines to isatin-derived ketimines hasbeen realized using a quinine-derived thiourea organocatalyst. The reaction affords chiral 3-amino-2-oxindoles bearing a quinoline moiety with a quaternary stereocenter in high yields (up to 98%) and excellent enantioselectivities (up to 99%). Moreover, we can extend this methodology for the enantioselective functionalization of 5-hydroxyisoquinoline. This methodology represents, to the best of our knowledge, the first enantioselective addition of hydroxyquinolines to imines.

    Vila Descals, Carlos Rendón-Patiño, Alejandra Montesinos Magraner, Marc Blay Llinares, Gonzalo Muñoz, M. Carmen Pedro, José Ramón 2018 Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines Advanced Synthesis & Catalysis 360 5 859 864
https://doi.org/10.1002/adsc.201701217

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