6533b82bfe1ef96bd128cd80

RESEARCH PRODUCT

Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetrasubstituted stereocenters.

Marc Montesinos-magranerGonzalo BlayCarlos VilaM. Carmen MuñozJosé R. PedroRuben CantonIsabel Fernández

subject

ChemistryOrganocatalysisIsatinIsatin-derived ketiminesEnantioselective synthesisAsymmetric synthesisGeneral ChemistryNaphtholsGeneral MedicineCatalysisStereocenterReaccions químiqueschemistry.chemical_compoundThioureaCatàlisiOrganocatalysisFISICA APLICADAOrganic chemistryPhenolsFriedel-Crafts reactionsQuímica orgànica

description

A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields (up to 99%) with excellent enantioselectivity (up to 99% ee). To the best of our knowledge, this transformation is the first highly enantioselective addition of naphthols to ketimines

yearjournalcountryeditionlanguage
2015-04-02Angewandte Chemie (International ed. in English)
10.1002/anie.201501273https://pubmed.ncbi.nlm.nih.gov/25845341