Selective synthesis of α-substituted β-keto esters from aldehydes and diazoesters on mesoporous silica catalysts

The titled reactions are effectively catalyzed on mesoporous silica MCM-41 but not on amorphous silica prepared from the same starting materials as those of MCM-41. The ordered porous structure was essential to generate the acid catalysis. Planting of Al or Ti ion improved not only the catalytic activity but also the tolerance to basic functional groups of substrates. The catalytic activity of Al- or Ti-MCM-41 was better than that of SnCl2 and NbCl5 in the homogeneous phase. In particular, Al (or Ti)-MCM-41 was characteristically active for the reaction of aldehydes with α-substituted diazoesters to give 2-substituted-3-oxo propionic acid esters.

Graphical abstractDownload full-size image