Abstract
Asymmetric induction by several chiral alcohols in the reaction of their bromoaceates with imines in the presence of activated Zn (Reformatsky reaction) was studied. Trans -2-phenylcyclohexanol 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.
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