Efficient and Stereodivergent Electrochemical Synthesis of Optically Pure Menthylamines

Abstract

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.