6533b7cffe1ef96bd125853c
RESEARCH PRODUCT
Gold-Catalyzed Intramolecular Hydroamination of o-Alkynylbenzyl Carbamates: A Route to Chiral Fluorinated Isoindoline and Isoquinoline Derivatives
Miguel A. MaestroPablo BarrioIgnacio IbáñezSilvia CatalanSantos Fusterosubject
Hydrocarbons FluorinatedMolecular StructureChemistryOrganic ChemistrySonogashira couplingStereoisomerismIsoindolineIsoindolesIsoquinolinesBiochemistryMedicinal chemistryCatalysischemistry.chemical_compoundCycloisomerizationNucleophileIntramolecular forceElectronic effectOrganic chemistryHydroaminationCarbamatesGoldPhysical and Theoretical ChemistryIsoquinolineAminesdescription
Enantiomerically pure fluorinated isoindoline and dihydroisoquinoline scaffolds have been prepared through a diastereoselective addition of fluorinated nucleophiles to Ellman’s N-(tert-butanesulfinyl)imines followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate. A more favored 5-exo-dig mechanism was observed mainly due to an electronic effect of the fluorinated group.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-01-01 |