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Magnesium-Promoted N-Selective Alkylation of Amides and Carbamates
Y.-Q. Fang*, M. M. Bio*, K. B. Hansen, M. S. Potter, A. Clausen
Amgen Inc., Cambridge, USA
21 December 2010 (online)
The authors describe a stereospecific N-alkylation of 2-pyridones, amides, and carbamates with chiral α-halocarboxylic acids 2. Stereospecific addition of oxygen nucleophiles to 2 are known, but secondary amide nucleophiles pose a bigger challenge in this reaction because of undesired competitive O-alkylation and base-promoted substrate or product racemization.