Dynamic kinetic resolution of α-chloro esters in asymmetric nucleophilic substitution using diacetone-D-glucose as a chiral auxiliary

Diacetone-D-glucose mediated dynamic kinetic resolution of α-chloro-α-aryl esters in nucleophilic substitution reactions has been investigated. Reactions of various amine nucleophiles in the presence of TBAI and DIEA can provide the substitution products 2–10 up to 97% yield and 97:3 dr. This simple procedure with easy removal of the chiral auxiliary provides a practical protocol for asymmetric syntheses of α-amino acid derivatives up to 97:3 er.