Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes: The role of arene-arene interactions

Abstract

The allylation of aromatic aldehydes with allyltrichlorosilanes can be catalyzed by the new Lewis basic organocatalyst quinox with high enantioselectivity for electron-poor aldehydes and low for their electron-rich congeners (see scheme). This behavior suggests an arene-arene interaction of the electron-rich catalyst with the incoming aldehyde as the main factor determining the enantiofacial selectivity.