Asymmetric Diels-Alder reactions on supported bis(oxazoline) catalysts

Periodic mesoporous ethane-silicas functionalized with sulfonic acid, cesium salts of 12-tungstophosphoric acid, activated silica, and SBA-15 have been used as solid supports for the immobilization of the bis(oxazoline) copper (II) catalyst via non-covalent interactions. These heterogeneous catalysts have been evaluated for the Diels-Alder reaction between 3-((E)-2-butenoyl)-1,3-oxazolin-2-one and cyclopentadiene. The performance of the catalyst relies on the nature of both the support and the anion on the surface of the support. The small number of the silanol groups on the support leads to poor enantloselectivity when SBA-15 is used.