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Keywords:

  • amines;
  • cations;
  • chiral pool;
  • electrochemistry;
  • lead
Thumbnail image of graphical abstract

The choice of cathodic material determines which epimer of menthylamine is preferentially formed in a stereodivergent electroorganic synthesis. As S. R. Waldvogel and co-workers report in their Communication on page 5564 ff., Hg cathodes provide selective access to (−)-menthylamine, whereas a decorated Pb cathode directs the formation of (M+)-neomenthylamine. A protective “glove” consisting of cationic additives controls the stereoselectivity, allows quantitative conversion, and avoids corrosion of the cathode.