6533b7d5fe1ef96bd1263d84

RESEARCH PRODUCT

Synthesis of Functionalized Indoles with a Trifluoromethy-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with beta-Trifluoromethyl-alpha, beta-enones

M. Carmen MuñozJosé R. PedroCarlos VilaGonzalo BlayIsabel Fernández

subject

IndolesHydrocarbons FluorinatedAlkylationEnonesStereoisomerismAlkylationElectrophilic aromatic substitutionLigandsMedicinal chemistryCatalysisCatalysisStereocenterchemistry.chemical_compoundAsymmetric catalysisOrganic chemistryCombinatorial Chemistry TechniquesAromatic substitutionFriedel–Crafts reactionTrifluoromethylMolecular StructureChemistryOrganic ChemistryEnantioselective synthesisStereoisomerismGeneral ChemistryKetonesCarbonFISICA APLICADAZirconiumFluorinated compounds

description

[EN] Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with beta-trifluoromethyl-alpha,beta-unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted alpha-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%.

yearjournalcountryeditionlanguage
2010-06-25
10.13039/501100004837http://hdl.handle.net/10251/150421