6533b850fe1ef96bd12a83a5
RESEARCH PRODUCT
Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates
Lidia HerreraSilvia CatalanRaquel RománSantos FusteroPablo BarrioIgnacio Ibáñezsubject
heterocyclesChemistryOrganic Chemistryasymmetric synthesisEnantioselective synthesischemistry.chemical_elementGeneral ChemistrycarbonylationpalladiumCatalysisCatalysisfluorineFluorineOrganic chemistryEnantiomeric excessCarbonylationRacemizationAminationPalladiumdescription
The asymmetric synthesis of fluorinated isoindolinones has been achieved by a palladium-catalyzed aminocarbonylation reaction of the corresponding -fluoroalkyl o-iodobenzylamines. A base-mediated anti -hydride elimination process was suggested to explain the partial erosion of the optical purity observed in some cases. This mechanistic rationale enabled the minimization of this partial racemization by fine-tuning the pK(a) of the base.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-01-01 |