手性磷酸催化下吲哚醇和吲哚烯参与的催化不对称反应

发布时间：2018-03-22 21:30

本文选题：手性磷酸　切入点：吲哚醇　出处：《江苏师范大学》2017年硕士论文　论文类型：学位论文

【摘要】：第一章,主要概括了手性磷酸催化下,吲哚醇、吲哚烯参与的催化不对称反应研究现状。同时,也介绍了这篇论文主要的研究内容和目标。第二章,我们实现了原子经济性的3-吲哚醇参与的催化不对称芳基化反应。通过靛红衍生的3-吲哚醇和3-甲基吲哚反应,合成了具有重要生物活性的3,3'-双吲哚取代的氧化吲哚产物,这种产物含有一个手性季碳中心,具有非常高的产率与优良的对映选择性。第三章,我们实现了2-吲哚醇作为3C合成子参与的催化不对称环加成反应。即在手性磷酸催化下,2-吲哚醇和甲亚胺叶立德发生[3+3]环加成反应,构建了手性四氢-γ-咔卟啉骨架,获得了较高的产率和优秀的对映选择性。该反应不仅实现了2-吲哚醇作为3C合成子在催化不对称环加成中的首次应用,而且实现了吲哚醇参与的反常区域选择性的不对称反应。更重要的是,这种方法还解决了2-吲哚醇参与的催化不对称环加成反应中存在的挑战,这将为研究2-吲哚醇参与催化不对称反应开辟一条新的道路。第四章,我们实现了醌亚胺单酮与烯烃的催化不对称[3+2]环化反应。采用3-吲哚烯作为底物,螺环手性磷酸作为高效的手性催化剂,实现了2,3-二氢苯并呋喃骨架的化学选择性、立体选择性构建。该反应为通过醌亚胺单酮参与的催化不对称反应来合成光学纯的含氧杂环化合物提供了很好的例子,同时也为构建光学纯的2,3-二氢苯并呋喃骨架提供了一种高效的有机催化的方法。
[Abstract]:In the first chapter, the research status of catalytic asymmetric reaction of indole and indole catalyzed by chiral phosphoric acid is summarized. At the same time, the main research contents and objectives of this paper are also introduced. We have realized the asymmetric arylation of 3-indolol with atomic economy. By the reaction of 3-indole and 3-methyl-indole derived from indirubin, we have synthesized the oxidation indole product with important biological activity. This product contains a chiral quaternary carbon center with very high yields and excellent enantioselectivity. We have realized the asymmetric cycloaddition of 2-indolol as 3C synthesizer, that is, the [33] cycloaddition reaction of 2-indolol and ylide was carried out under the catalysis of chiral phosphoric acid, and the chiral tetrahydro- 纬 -carboloporphyrin framework was constructed. High yield and excellent enantioselectivity were obtained. This reaction not only realized the first application of 2-indole as 3C synthesizer in catalytic asymmetric cycloaddition. Moreover, abnormal region-selective asymmetric reactions involving indole were realized. More importantly, this method also solved the challenges in the catalytic asymmetric cycloaddition reaction involving 2-indole. In chapter 4, we realized the asymmetric [32] cyclization of quinone imine monoketone with olefin. As a highly efficient chiral catalyst, spirocyclic chiral phosphoric acid has achieved the chemical selectivity of 2H 3- dihydrobenzofuran skeleton. Stereoselective construction. This reaction provides a good example for the synthesis of optically pure oxygen-containing heterocyclic compounds by catalytic asymmetric reactions involving quinone imine monone. At the same time, it provides an efficient organic catalytic method for the construction of optical pure 2H 3- dihydrobenzofuran skeleton.
【学位授予单位】：江苏师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251

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