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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z51737_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.