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从二肽合成的手性离子液作为有机催化剂在Michael加成反应和Aldol缩合反应中的应用

hiral Ionic Liquids Based on Dipeptides as Organocatalysts for Asymmetric Michael Addition and Aldol reaction

中文摘要英文摘要

本文以1-丁基-3甲基咪唑氯化物([Bmim]Cl)作为反应起始原料与NaOH在无水乙醇中反应得产物[Bmim]OH乙醇溶液,然后与二肽进行中和合成三种新型的手性离子液的方法,这种方法不仅简单,便利而且产率高,是首次报道的以二肽作为阴离子的手性离子液。同时研究了这些手性离子液作为有机催化剂在环己酮和β-硝基苯乙烯的不对称Michael加成反应以及环己酮和对硝基苯甲醛的Aldol缩合反应中的应用情况,都能顺利的得到相应的产物,光学活性最高可以达到92%。

1-Butyl-3-methylimidazolium chloride ([Bmim]Cl) was employed as a starting material to react with NaOH in anhydrous ethyl alcohol. The desired 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) ethanol solutuion could be obtained. The [Bmim]OH ethanol solution was added dropwise to a slightly excess equimolar dipeptide ethanol solution to give three kinds of chiral ionic liquids. It is a simple and convenient method in excellent yields. It is the first report on the synthesis of new chiral ILs based on dipeptide anions. The application of the new chiral ionic liquids as organocatalysts for asymmetric Michael addition of cyclohexanone to β-nitrostyrene and Aldol reaction of cyclohexanone to p-nitrobenzaldehyde has been studied. Reasonable yields and up to 92%ee were obtained under these reaction conditions.

王治明、程冬萍、包伟良

有机化学工业

手性离子液Michael加成ldol缩合

hiral Ionic LiquidsMichael additionldol reaction

王治明,程冬萍,包伟良.从二肽合成的手性离子液作为有机催化剂在Michael加成反应和Aldol缩合反应中的应用[EB/OL].(2009-01-07)[2025-08-23].http://www.paper.edu.cn/releasepaper/content/200901-280.点此复制

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