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Prof. Anna Iuliano

Synthesis of novel Chiral Ionic Liquids (CILs) from chiral pool and their application in Enantioselective Electroanalysis (Ee) and Gas Chromatography (GC)

Enantioselective electroanalysis (Ee) is an analytic technique that, in principle, is able to give qualitative and quantitative information on the enantiomers of a compound without the need of preliminary purifications. In the last years this technique has been developed using two main approaches: i) use of chiral electrodes; ii) use of enantiopure chiral medias (solvents or additives). Nowadays Ee is still regarded as an immature technique, given the lack of chiral selectors of general use and practical protocols. Recently, good results have been obtained using “inherently chiral” molecules,1,3 compounds where the chirality does not arise from stereogenic centres or axes, but from a twisting of the molecule in 3-D space. Ionic liquids are very useful media for electrochemical processes, given that they can be regarded at the same time as solvents and electrolytes and given that these compounds organize themselves in well-defined structures at the electrode-solution interface; this property, in principle, can also help the enantiodiscrimination of chiral ionic liquids (CILs). As a matter of fact, in few recents works the use of CILs in Ee was successful, even if only on a little number of analytes. Enantioselective GC is one of the fastest and most robust protocols to separate enantiomers, but a limited number of chiral selectors are available, due the scarce thermic stability of organic compounds. Ionic liquids and CILs are often characterised by thermic stability higher than other classes of organic compounds5 and for this reason they can be considered promising selectors for enantioselective GC. This PhD project aims to develop a library of novel CILs starting from economic enantiopure natural compounds, such as isohexides (derived from natural carbohydrates) and bile acids, to develop new chiral selectors that could be used in various application, from Ee to GC.

V. Zullo, A. Iuliano, “Rh‐catalyzed enantioselective conjugate addition of arylboronic acids to 3‐arylpropenoates: enantioselective synthesis of (R)‐Tolterodine”, EurJoc, doi 10.1002/ejoc.201801690

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