A. Kubo, H. Kubota, Masami Takahashi
Jul 8, 1996
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron Letters
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 (4S)-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.