We thank Dr. Nils Trapp for the X-ray analysis and the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (DFG) for financial support.
Convenient Titanium(III)-Catalyzed Synthesis of Cyclic Aminoketones and Pyrrolidinones—Development of a Formal [4+1] Cycloaddition†
Article first published online: 5 JUN 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 28, pages 7131–7134, July 8, 2013
How to Cite
Frey, G., Luu, H.-T., Bichovski, P., Feurer, M. and Streuff, J. (2013), Convenient Titanium(III)-Catalyzed Synthesis of Cyclic Aminoketones and Pyrrolidinones—Development of a Formal [4+1] Cycloaddition. Angew. Chem. Int. Ed., 52: 7131–7134. doi: 10.1002/anie.201302460
- Issue published online: 4 JUL 2013
- Article first published online: 5 JUN 2013
- Manuscript Received: 24 MAR 2013
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft
- radical reactions;
Have it both ways: α-Aminated ketones can be prepared by the titanium(III)-catalyzed reductive radical cyclization of iminonitriles. Depending on the position of the nitrile at the imine carbon or nitrogen, cyclic aminoketones or pyrrolidin-3-ones with a tetrasubstituted α-carbon can be formed in up to quantitative yield. In the latter case, the imine condensation and TiIII catalysis correspond to a formal [4+1] cycloaddition.