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An analytical HPLC method using CHIREX (S)-LEU/(S)-α-NEA column was developed for the determination of the enantiomeric excesses of N-protected (S)-3-hydroxyglutarimides. Using this method, detailed studies on the base-promoted ring-expansion reaction of the amidolactones, derived from l-glutamic acid, were undertaken. © 2005 Wiley-Liss, Inc. Chirality 17:595–599, 2005.