Magnesium-Promoted N-Selective Alkylation of Amides and Carbamates

Significance

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.