We thank the University of Glasgow, the Socrates Exchange program, and Dr. Alfred Bader for financial support.
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Communication
Quinox, a Quinoline-Type N-Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions†
Article first published online: 7 AUG 2003
DOI: 10.1002/anie.200351737
Copyright © 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Malkov, A. V., Dufková, L., Farrugia, L. and Kočovský, P. (2003), Quinox, a Quinoline-Type N-Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions. Angew. Chem. Int. Ed., 42: 3674–3677. doi: 10.1002/anie.200351737
- †
Publication History
- Issue published online: 7 AUG 2003
- Article first published online: 7 AUG 2003
- Manuscript Received: 24 APR 2003
Keywords:
- allylation;
- arenes;
- asymmetric catalysis;
- O ligands;
- organocatalysis
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.