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Efficient and Stereodivergent Electrochemical Synthesis of Optically Pure Menthylamines†
Article first published online: 12 MAY 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 24, pages 5564–5567, June 6, 2011
How to Cite
Kulisch, J., Nieger, M., Stecker, F., Fischer, A. and Waldvogel, S. R. (2011), Efficient and Stereodivergent Electrochemical Synthesis of Optically Pure Menthylamines . Angew. Chem. Int. Ed., 50: 5564–5567. doi: 10.1002/anie.201101330
- Issue published online: 1 JUN 2011
- Article first published online: 12 MAY 2011
- Manuscript Received: 22 FEB 2011
- chiral pool;
The cathode directs the way to the epimeric menthylamines. The reduction of menthone oxime on a Hg cathode generates (−)-menthylamine as the major product, whereas a Pb cathode gives access to (+)-neomenthylamine (see scheme). In situ decoration of the Pb cathode by small amounts of additives results in clean and quantitative conversions. Furthermore, Pb corrosion is completely prevented in this practical method.