Synthesis of an optically pure 3-unsubstituted β-lactam using an asymmetric reformatsky reaction and its conversion to cholesterol absorption inhibitors

Article abstract of DOI:10.1016/0040-4039(96)00764-2

Asymmetric induction by several chiral alcohols in the reaction of their bromoacetates with imines in the presence of activated Zn (Reformatsky reaction) was studied. Trans-2-phenlcyclohexanol and phenyl menthol gave β- lactam 9, obtained by cyclizing the diastereoisomeric β-aminoesters 8, in > 99%ee. The resulting chiral 3-unsubstituted azetidin-2-one 9 was converted to 3-substituted products 11, 12, and 13 which exhibit cholesterol absorption inhibitory activity.