These authors contributed equally to this work.
Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes†
Article first published online: 10 SEP 2009
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 42, pages 7892–7894, October 5, 2009
How to Cite
Galzerano, P., Pesciaioli, F., Mazzanti, A., Bartoli, G. and Melchiorre, P. (2009), Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes. Angew. Chem. Int. Ed., 48: 7892–7894. doi: 10.1002/anie.200903803
This work was supported by Bologna University and by MIUR National Project “Stereoselezione in Sintesi Organica”.
- Issue published online: 30 SEP 2009
- Article first published online: 10 SEP 2009
- Manuscript Received: 11 JUL 2009
- Bologna University
- cascade reactions;
- molecular complexity;
- quaternary stereocenters
Time to α-branch out! The first highly enantioselective aminocatalytic activation of α-substituted α,β-unsaturated aldehydes is presented. The chiral primary amine 1 selectively activates α-branched enals toward a well-defined iminium ion/enamine reaction sequence for both Friedel–Crafts/amination and sulfa-Michael/amination cascades. The valuable multifunctional products, having two contiguous sterocenters, are isolated in high enantiomeric purity.