Quinox, a Quinoline‐Type <i>N</i>‐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.