The Role of Binding Constants in the Efficiency of Chiral Catalysts Immobilized by Electrostatic Interactions: The Case of Azabis(oxazoline)–Copper Complexes

As shown by theoretical calculations, azabis(oxazoline)-copper complexes are considerably more stable than the analogous bis(oxazoline)-copper complexes. This enhanced stability allows them to be efficiently immobilized by means of electrostatic interactions to different anionic supports, such as clays and nafion-silica nanocomposites, without the loss of a ligand, as is observed for bis(oxazolines). As a result, enantioselectivities of around 90 % ee are obtained in the cyclopropanation reaction between styrene and ethyl diazoacetate. Moreover, the solid catalyst is easily recoverable.