Dynamic kinetic resolution by stereospecific amination utilizing 2-oxoimidazolidine-4-carboxylate as a novel chiral auxiliary

Article abstract of DOI:10.1016/S0040-4039(00)78458-9

A novel type of dynamic kinetic resolution by stereospecific amination was exploited utilizing 2-oxoimidazolidine-4-carboxylate 1 as a chiral auxiliary. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carbo xylate (2) with benzylamine in HMPA in the presence of K₂CO₃ or Et₃N at 25°C predominantly afforded tert-butyl (4S)-1-methyl-3-((2R)-2-benzylaminopropionyl)-2-oxoimidazolidi ne-4-carboxylate ((S,R)-4) in nearly quantitative yield.