Abstract
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 (4 S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate ( 2) with benzylamine in HMPA in the presence of K 2CO 3 or Et 3N at 25°C predominantly afforded tert-butyl (4 S)-1-methyl-3-((2 R)-2-benzylaminopropionyl)-2-oxoimidazolidine-4-carboxylate (( S,R)- 4) in nearly quantitative yield.
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