Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates. Issue 32 (29th June 2015)

• Record Type: Journal Article
• Authors: Barrio, Pablo; Ibáñez, Ignacio; Herrera, Lidia; Román, Raquel; Catalán, Silvia; Fustero, Santos
• Is Part Of: Chemistry. Volume 21:Issue 32(2015)
• Page Start: 11579
• Page End: 11584
• Publication Date: 2015-06-29
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201500773
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The asymmetric synthesis of fluorinated isoindolinones has been achieved by a palladium‐catalyzed aminocarbonylation reaction of the corresponding α‐fluoroalkyl <italic>o</italic>‐iodobenzylamines. A base‐mediated <italic>anti</italic> 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 p<italic>K</italic>_a of the base.</p> </abstract>