trans-(3 S)-Amino piperidines bearing various alkyl and aryl substituents at the C-4 position were synthesized via a ring-closing metathesis reaction. The absolute stereochemistry was controlled using a protected d-serine as a starting material. Stereoselective hydrogenation of allylamines provided trans-(3 S)-amino-(4 R)-alkyl-and-(4 S)-aryl-piperidines. This procedure presents the first method for the asymmetric synthesis of 4-substituted 3-amino ...