Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OiPr)3/amide-based ligand catalyst

A catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr(OiPr)3 and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding.