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Andrei V. Malkov, Lenka Dufková, Louis Farrugia and Pavel Kočovský Quinox, a Quinoline-Type N-Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions Angewandte Chemie International Edition 42

Article first published online: 7 AUG 2003 | DOI: 10.1002/anie.200351737

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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.

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