Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates |
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| Authors: | Dr. Pablo Barrio Ignacio Ibáñez Lidia Herrera Dr. Raquel Román Dr. Silvia Catalán Prof. Dr. Santos Fustero |
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| Affiliation: | 1. Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain;2. Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia (Spain) |
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| 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. |
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| Keywords: | asymmetric synthesis carbonylation fluorine heterocycles palladium |
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