Asymmetric hydrogenation of 2-aryl-3-phthalimidopyridinium salts catalyzed by the Ir/SegPhos catalytic system was described, leading to the corresponding chiral piperidinederivatives bearing two contiguous chiral centers, with high levels of enantioselectivities and diastereoselectivities. A gram-scale experiment has demonstrated the utility of this approach. The phthaloyl group could be easily removed