Cu-Catalyzed N-Arylation of Oxazolidinones: An Efficient Synthesis of the κ-Opioid Receptor Agonist CJ-15161
The Journal of Organic Chemistry2005Vol. 71(3), pp. 1258–1261
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Arun K. Ghosh, Janice E. Sieser, Stéphane Caron, Michel Couturier, Kristina Dupont‐Gaudet, Mélina Girardin
Abstract
An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported. The conditions allow the use of copper and can be used to prepare enantiopure N-aryl beta-amino alcohols. A short, scalable synthesis of CJ-15,161 is also reported. The required amines were obtained from the precursor alpha-amino acids or, more conveniently, from the corresponding 1,2-amino alcohols.
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