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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
  • 期刊名称:高等学校化学学报, 2009,30(1): 1-4.
  • 时间:0
  • 分类:O621[理学—有机化学;理学—化学]
  • 作者机构:[1]河北师范大学化学与材料科学学院,石家庄050016
  • 相关基金:国家自然科学基金(批准号:20772021)和河北省自然科学基金(批准号:B2007000239)资助.
  • 相关项目:可溶性1,5-苯并硫氮杂卓类化合物的设计、合成及生物活性研究
中文摘要:

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.

英文摘要:

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%.

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