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Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34
Graphical Abstract
Scheme 1: Structural features of 8-substituted menthylamines 1.
Scheme 2: Synthetic strategies to menthylamines.
Scheme 3: Stereoselective synthesis of 8-substituted (1R,3R,4S)-menthylamines.
Scheme 4: Influence of the cathode system onto the stereoselectivity of the reduction of (1R,4S)-menthone oxi...
Scheme 5: Preparation of 8-substituted (1R)-menthones 6 and the corresponding oximes 7.
Scheme 6: Influence of cathode material on the preparation of (1R,3R,4S)-menthylamine 8a.
Scheme 7: Protection of the oxime functionality in 7c due to the sterically demanding diphenyl moiety in 8-po...
Scheme 8: Separation of the diastereomeric 8-substituted menthylamines by crystallization of their hydrochlor...