Quinox, a Quinoline-Type N-Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions


  • We thank the University of Glasgow, the Socrates Exchange program, and Dr. Alfred Bader for financial support.


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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.