Stereodivergent catalysis is of great importance, as it can allow efficient access to all possible stereoisomers of a given product with multiple stereocenters from the same set of starting materials. We report herein the first diastereodivergent [3 + 2] annulation of aromatic aldimines with alkenes via C-H activation by half-sandwich rare-earth catalysts. This protocol provides an efficient and general route for the selective synthesis of both trans and cis diastereoisomers of multisubstituted 1-aminoindanes from the same set of aldimines and alkenes, featuring 100% atom efficiency, excellent diastereoselectivity, broad substrate scope, and good functional group compatibility. The diastereodivergence is achieved by fine-tuning the sterics or ligand/metal combination of the half-sandwich rare-earth metal complexes.