6533b7d2fe1ef96bd125e2e9
RESEARCH PRODUCT
Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an Aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines
José R. PedroMarc Montesinos-magranerCarlos VilaM. Carmen MuñozGonzalo BlayAlejandra Rendón-patiñosubject
biology010405 organic chemistryIsatinIsatin-derived ketiminesQuinolineQuinolineThioureaEnantioselective synthesisGeneral Chemistry010402 general chemistrybiology.organism_classification01 natural sciencesReaccions químiques0104 chemical sciencesAsymmetric organocatalysischemistry.chemical_compoundCatàlisichemistryFISICA APLICADAOrganic chemistryHydroxyquinolinesFriedel-Crafts reactionValenciaFriedel–Crafts reactiondescription
[EN] 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-01-01 | Advanced Synthesis & Catalysis |