Non-covalent chiral organocatalysis uses water as a solvent

26-Jul-2010 - Germany

The first example of Brønsted acid asymmetric catalysis in aqueous solution is reported by Magnus Rueping and Thomas Theissman at Aachen University, Germany.

Using a chiral phosphoric acid catalyst Rueping demonstrates highly enantioselective hydrogenation of quinolines in water, a reaction previously considered impossible to carry out in water. The phosphoric acid forms a hydrogen bond with the quinoline, and directs the dihydropridine hydride donor to a particular face. This hydrogen-bonding catalysis occurs despite the fact that water is an excellent hydrogen donor itself, due to the phenomenon of ‘hydrophobic hydration’.

Rueping is confident that similar organocatalysis reactions could be carried out on a large industrial scale, which could remove the need for elimination of hazardous chlorinated or organic solvents.

Original publication: Magnus Rueping and Thomas Theissmann, Chem. Sci. 2010

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