This work was supported by the Fonds der Chemischen Industrie and the University of Mainz. We thank H. Kolshorn for performing the 2D-NMR experiments and the NOE measurements.
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Communication
An Aldimine Cross-Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2-Diamines†
Article first published online: 29 JUL 2005
DOI: 10.1002/anie.200501705
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 44, Issue 35, pages 5662–5664, September 5, 2005
Additional Information
How to Cite
Kison, C., Meyer, N. and Opatz, T. (2005), An Aldimine Cross-Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2-Diamines. Angewandte Chemie International Edition, 44: 5662–5664. doi: 10.1002/anie.200501705
- †
Publication History
- Issue published online: 1 SEP 2005
- Article first published online: 29 JUL 2005
- Manuscript Revised: 17 MAY 2005
- Manuscript Received: 15 FEB 2005
- Abstract
- Article
- References
- Cited By
Keywords:
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C coupling; - carbanions;
- diamines;
- reduction;
- umpolung
Graphical Abstract
No protecting groups are required for the cross-coupling of N-monosubstituted α-aminonitriles with imines. Depending on the workup procedure, highly substituted unsymmetrical 1,2-diamines or 1,2-diimines can be prepared in a one-pot procedure. The diastereoselective reduction of the diimines furnishes either the syn- or the anti-configurated diamines (see scheme).