title: Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates.
abstract: 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.
authors.affiliation: Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain. pablo.barrio@uv.es.
authors.forename: Pablo
authors.initials: P
authors.lastname: Barrio
authors.affiliation: Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia (Spain).
authors.forename: Ignacio
authors.initials: I
authors.lastname: Ibáñez
authors.affiliation: Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain.
authors.forename: Lidia
authors.initials: L
authors.lastname: Herrera
authors.affiliation: Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain.
authors.forename: Raquel
authors.initials: R
authors.lastname: Román
authors.affiliation: Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia (Spain). silvia.catalan@uv.es.
authors.forename: Silvia
authors.initials: S
authors.lastname: Catalán
authors.affiliation: Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain. santos.fustero@uv.es.|Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia (Spain). santos.fustero@uv.es.
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
keywords: asymmetric synthesis; carbonylation; fluorine; heterocycles; palladium