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Palladium-Catalyzed Synthesis of N-Aryloxazolidinones from Aryl Chlorides

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journal contribution
posted on 24.05.2003, 00:00 by Arun Ghosh, Janice E. Sieser, Maxime Riou, Weiling Cai, Luis Rivera-Ruiz
An efficient method for intermolecular N-arylation of oxazolidinones using Pd2dba3 and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl β-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.