We thank Dr. D. Jeannerat and A. Pinto for NMR measurements, the University of Geneva, and the Swiss National Science Foundation for financial support. We also acknowledge the contributions of the Sciences Mass Spectrometry (SMS) platform at the Faculty of Sciences (University of Geneva), and the CRCMM and the Spectropole at the University of Aix-Marseille for computer time and use of the VCD facility, respectively.
One-Step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases†
Article first published online: 18 MAR 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 16, pages 3677–3680, April 11, 2011
How to Cite
Sharma, A., Guénée, L., Naubron, J.-V. and Lacour, J. (2011), One-Step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases. Angew. Chem. Int. Ed., 50: 3677–3680. doi: 10.1002/anie.201100134
- Issue published online: 5 APR 2011
- Article first published online: 18 MAR 2011
- Manuscript Received: 7 JAN 2011
- University of Geneva
- Swiss National Science Foundation
- diazo compounds;
- Tröger bases
Bridging the gap: Configurationally stable ethano-bridged Tröger bases have been prepared in a single step by the direct rhodium(II)-catalyzed reaction of methano-bridged Tröger bases and diazo esters (see scheme). The process is general, enantiospecific, diastereoselective (with introduction of a new quaternary carbon center), and regioselective.