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Efficient and Stereodivergent Electrochemical Synthesis of Optically Pure Menthylamines
Author(s) -
Kulisch Jörn,
Nieger Martin,
Stecker Florian,
Fischer Andreas,
Waldvogel Siegfried R.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101330
Subject(s) - cathode , electrochemistry , reduction (mathematics) , oxime , chemistry , materials science , combinatorial chemistry , nanotechnology , chemical engineering , organic chemistry , mathematics , electrode , engineering , geometry
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.