3-(3S-叔丁氧基)丁二酰亚胺基β-内酰胺的合成及反应的立体选择性  

Synthesis of 3-(3S-t-Butoxyl) succinimidyl-β-lactams and the Stereoselectivity of the Reaction

作　　者：张萍[1] 刘娜[1] 王兰芝[1] 李媛[1] 

机构地区：[1]河北师范大学化学与材料科学学院,石家庄050016

出　　处：《高等学校化学学报》2009年第1期90-94,共5页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20772021);河北省自然科学基金(批准号:B2007000239)资助

摘　　要：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%.

关 键 词：Β-内酰胺 SCHIFF碱 顺反异构选择性 非对映异构选择性 立体选择性 

分 类 号：O621[理学—有机化学]