Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines

• Carolin Edinger,
• Jörn Kulisch and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34

• Carolin Edinger Jorn Kulisch Siegfried R. Waldvogel Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany 10.3762/bjoc.11.34 Abstract The electrochemical generation of menthylamines from the corresponding menthone oximes equipped with an

• additional substituent in position 8 is described. Due to 1,3-diaxial interactions a pronounced diastereoselectivity for the menthylamines is found. Keywords: cathodic reduction; chiral amines; electrosynthesis; menthylamines; oximes; Introduction Optically active amines serve as powerful and versatile

• substituents R create a molecular U-turn (see Scheme 1). However, while optically pure menthol derivatives play a significant role in organic synthesis [28], menthylamines have only been used in a few situations, which is attributable to their rather poor availability in optically pure manner. Among the