1269822-85-6Relevant academic research and scientific papers
Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates
Barrio, Pablo,Ibá?ez, Ignacio,Herrera, Lidia,Román, Raquel,Catalán, Silvia,Fustero, Santos
, p. 11579 - 11584 (2015/08/03)
The asymmetric synthesis of fluorinated isoindolinones has been achieved by a palladium-catalyzed aminocarbonylation reaction of the corresponding α-fluoroalkyl o-iodobenzylamines. A base-mediated anti β-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 pKa of the base.
Gold-catalyzed intramolecular hydroamination of o-alkynylbenzyl carbamates: A route to chiral fluorinated isoindoline and isoquinoline derivatives
Fustero, Santos,Ibá?ez, Ignacio,Barrio, Pablo,Maestro, Miguel A.,Catalán, Silvia
supporting information, p. 832 - 835 (2013/03/28)
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.
