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Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an Aza‐Friedel‐Crafts Alkylation with Isatin‐derived Ketimines
Author(s) -
Vila Carlos,
RendónPatiño Alejandra,
MontesinosMagraner Marc,
Blay Gonzalo,
Muñoz M. Carmen,
Pedro José R.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701217
Subject(s) - enantioselective synthesis , chemistry , stereocenter , isatin , thiourea , moiety , organocatalysis , alkylation , organic chemistry , quinoline , combinatorial chemistry , surface modification , catalysis
Abstract A highly enantioselective addition of hydroxyquinolines to isatin‐derived ketimines has been 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.