Abstract
A Highly stereoselective Gabriel reaction via dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary was exploited. The reaction of tert-butyl (4 S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate ( 2a) with potassium phthalimide at room temperature predominantly afforded tert- butyl (4S)-1- methyl-3-((2S)-2-( phthaloylamino)propionyl)-2-oxoimidazolidine-4-carboxylate ((S,S)- 5a) in a good yield which was derived to l- alanine derivative ( 7) by removal of the chiral auxiliary.
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