3β-(3,4-Disubstituted succinimido)azetidinones are provided via stereoselective cycloaddition of imines with chiral auxiliary 3,4-disubstituted succinimidoacetyl chlorides. The chiral auxiliary e.g., 3S,4S-dibenzoyloxy-and 3S,4S-diacetoxysuccinimidoacetyl chloride, is obtained from tartaric acid via anhydride and imide formation with retention of chirality. The chiral azetidinones obtained are useful intermediates to β-lactam antibacterial compounds.
3β-(3,4-二取代琥珀
酰亚胺基)氮杂
环丁酮是通过
亚胺与手性辅助剂 3,4-二取代琥珀
酰亚胺基
乙酰氯的立体选择性环加成反应而获得的。 手性辅助剂,如 3S,4S-二苯甲酰氧基和 3S,4S-
二乙酰氧基琥珀
酰亚胺基
乙酰氯,是从
酒石酸中通过酸酐和
亚胺的形成而获得的,并保留了手性。 所获得的手性氮杂
环丁酮是β-内酰胺类抗菌化合物的有用中间体。