以S-苹果酸作为手性诱导试剂,通过Staudinger反应,合成了8个具有光学活性的新型的β-内酰胺衍生物,通过^1H NMR,IR谱和元素分析对其结构进行了表征,用^1H NMR,2D NMR谱和单晶X射线衍射法研究了该反应的立体选择性.结果表明,S-苹果酰亚胺乙酰氯(三乙胺存在下)与Schiff碱的反应具有高度的顺反异构选择性,反式β-内酰胺是唯一产物;该反应的非对应异构选择性较好,d.e.值在28%-70%之间.
S-Malic acid is the chiral induction agent widely used in organic synthesis. In order to investigate the stereoselective synthesis of β-lactams, eight new 3-(3S-t-butoxyl)succinimidyl-β-lactam derivatives 2a- 2h were obtained by Staudinger reaction using S-malic acid as the chiral induction agent and their structures were confirmed by ^1H NMR, IR and elemental analysis. The stereochemistry of the reaction was also investigated by the ^1H NMR, 2D NMR and X-ray diffraction analyses methods. The results indicate that the reaction of 3-(3S-t-butoxyl) succinimidyl acetyl chloride with imines (under Et3N) showing very good cis/trans stereoselectivity, and the trans-β-lactam is the only product. The diastereomeric selectivity is also good, the d.e. is between 28%-70%.