An efficient two‐step procedure for the synthesis of enantiomerically pure, benzene nucleus‐substituted 1‐phenylethylamines 1 is described, with predictable absolute configuration at the stereogenic center: Imine formation from the substituted acetophenones 6 with (S)‐ or (R)‐1‐phenylethylamine [(S)‐7 or (R)‐7] and subsequent hydrogenation of the resulting Schiff bases 8 over Raney nickel leads to the secondary amines 9 and 10 in high diastereoselectivities. These dibenzylamines are cleaved regioselectively, usually next to the less substituted aromatic ring, giving the desired chiral 1‐phenylethylamines 1 in high yields and enantiomeric purities. Scope and limitations of this new and facile approach to the versatile building blocks 1 are reported.
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