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Investigating ionic effects applied to water based organocatalysed aldol reactions

Delaney, Joshua P. and Henderson, Luke C. 2011, Investigating ionic effects applied to water based organocatalysed aldol reactions, International journal of molecular sciences, vol. 12, no. 12, pp. 9083-9094.

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Title Investigating ionic effects applied to water based organocatalysed aldol reactions
Author(s) Delaney, Joshua P.
Henderson, Luke C.
Journal name International journal of molecular sciences
Volume number 12
Issue number 12
Start page 9083
End page 9094
Total pages 12
Publisher Molecular Diversity Preservation International (M D P I)
Place of publication Basel, Switzerland
Publication date 2011-12
ISSN 1422-0067
Keyword(s) aldol
Ionic solution
organocatalysis
water
Summary 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.
Language eng
Field of Research 039999 Chemical Sciences not elsewhere classified
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Persistent URL http://hdl.handle.net/10536/DRO/DU:30044387

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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Citation counts: TR Web of Science Citation Count  Cited 3 times in TR Web of Science
Scopus Citation Count Cited 2 times in Scopus
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