Investigating ionic effects applied to water based organocatalysed aldol reactions.
Investigating ionic effects applied to water based organocatalysed aldol reactions.
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DOI：
10.3390/ijms12129083
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发表时间：
2011
影响因子：
5.6
通讯作者：
Henderson LC
中科院分区：
文献类型：
--
作者：
Delaney JP;Henderson LC
在本实验室研制的一种高活性的c2对称双丙酰胺有机催化剂催化下，研究了各种普通盐的饱和水溶液对水性醛醇反应的影响。对于环己酮和4-硝基苯甲醛之间的醛醇反应，去离子水始终是盐溶液的优越介质，尽管可以观察到阴离子大小的增加和对映体过量的减少有一定的相关性。此外，当使用自来水时观察到的催化剂活性的完全抑制可以通过在反应开始前将乙二胺四乙酸酯（EDTA）包合到水介质中来缓解。这些反应条件的延伸表明，这些离子效应在不同情况下的变化取决于酮/醛的组合。
Saturated aqueous solutions of various common salts were examined for their effect on aqueous aldol reactions catalysted by a highly active C2-symmetric diprolinamide organocatalyst developed in our laboratory. With respect to the aldol reaction between cyclohexanone and 4-nitrobenzaldehyde, deionised water was always a superior medium to salt solutions though some correlation to increasing anion size and depression in enantiomeric excess could be observed. Additionally, the complete inhibition of catalyst activity observed when employing tap water could be alleviated by the inclusion of ethylenediaminetetraacetate (EDTA) into the aqueous media prior to reaction initiation. Extension of these reaction conditions demonstrated that these ionic effects vary on a case-to-case basis depending on the ketone/aldehyde combination.
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