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Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions
Chemistry and Systems Biology, Strategic Research Center for Biotechnology, Deakin University, Waurn Ponds Campus, Geelong, Victoria 3216, Australia
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Received: 28 October 2011; in revised form: 26 November 2011 / Accepted: 29 November 2011 / Published: 7 December 2011
Abstract: 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.
Keywords: ionic solution; organocatalysis; aldol; water
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MDPI and ACS Style
Delaney, J.P.; Henderson, L.C. Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions. Int. J. Mol. Sci. 2011, 12, 9083-9094.
Delaney JP, Henderson LC. Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions. International Journal of Molecular Sciences. 2011; 12(12):9083-9094.
Delaney, Joshua P.; Henderson, Luke C. 2011. "Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions." Int. J. Mol. Sci. 12, no. 12: 9083-9094.