The base-catalyzed ring opening of 4-(4'-hydroxyphenyl)-azetidine-2-ones with potassium tert-butoxide in the presence of tert-butyl methyl malonate gave 1,3,4,5-substituted glutarimides in a simple and efficient manner. The glutarimides were formed stereo selectively depending on the size or the 3-substituent of the beta-lactam. (C) 2002 Elsevier Science Ltd. All rights reserved.