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题名 LiCl催化的2-四氢糠酸甲酯烯醇硅醚与醛的Aldol反应
姓名 潘祥
院系 生命科学学院
专业 生物化学与分子生物学
学位名称 理学硕士
外文题名 The Aldol Reaction of the Silyl Enol Ether of Methyl Tetrahydrofuran-2-Carboxylate with Aldehyde Catalyzed by LiCl
第一导师姓名 达朝山
关键词 2-四氢糠酸甲酯;烯醇硅醚;Aldol反应;LiCl;β-羟基酯
外文关键词 Methyl tetrahydrofuran-2-carboxylate;silyl enol ether;Aldol reaction;LiCl;β-Hydroxy ester
学科 理学
摘要 在有机化学领域,Aldol反应的发现具有重要的意义,其中烯醇硅醚对醛类的加成,是应用Aldol反应合成β-羟基酮或者酯最常用、最有效的方法之一。以往的工作是利用酮或者酯直接和醛类的加成来得到β-羟基酮或者酯,但是像含氧杂环类亲核试剂的Aldol反应,其副反应比较多,产率比较低。近年来兴起的路易斯酸催化的烯醇硅醚和醛类的加成反应较好地克服了这一缺点,极大提高了Aldol反应的适用性,成为了新的研究热点。 经过尝试三种路易斯酸的催化效果,和各种条件的优化,我们发现廉价易得的路易斯酸(LiCl)可以较好地催化2-四氢糠酸甲酯的烯醇硅醚与醛类的Aldol加成,并且都得到了预想的加成产物β-羟基酯,产率最高达到了92%。该方法对底物醛类都表现出较好的适用性。在反应体系中只需要添加催化剂量的路易斯酸即可完成烯醇硅醚对醛类的高效加成,较高产率的获得醛和2-四氢糠酸甲酯烯醇硅醚的加成产物,和一般的非亲核性强碱介导的酯和醛的直接加成相比,减少了副产物的产生,控制了反应的专一性。该反应体系的条件比较温和,操作易于控制,不需要在很低的温度条件下进行,对于我们进一步深入研究Mukaiyama Aldol反应具有十分重要的意义。
外文摘要 In the field of organic chemistry, the discovery of the Aldol reaction has the great significance. The addition of the silyl enol ether to aldehydes is the common and effective way to synthesize the β-hydroxy ketone or ester. In previous works the direct addition of ketone or ester to aldehydes was used to get the β-hydroxy ketone or ester. However, some nucleophiles such as oxygen-containing heterocyclic compounds are tough reagents for the Aldol reaction with quite low yield. The advancement appeared in recent years due to the rise of lewis acid catalysis in the addition of silyl enol ether to aldehydes. It has currently become a hot spot research because it greatly increased a number of Aldol reactions. In our study, we tried to use Lewis acid LiCl to catalyse the aldol reaction of the silyl ether of methyl tetrahydrofuran-2-carboxylate with aldehydes, after optimization of reaction conditions, we found that in the catalysis of LiCl the Aldol addition of the Silyl enol ether of methyl tetrahydrofuran-2- carboxylate to the aldehyde couild be performed in high yield. The highest yield was up to 92%. Furthermore, the substrate scope is extensive in this study. In addition, the reaction system could be conducted in the relatively mild conditions. The operation is easy.
研究领域 手性药物
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