The stereoselective synthesis of octahydroindole derivatives is reported according to 3–4-step sequences. The strategy relies on our previously developed catalytic asymmetric C(sp3)–H amination reaction. Its application to cyclic enol triflates affords allylic amines in good yields and stereoselectivity. The C–H functionalization step, then, is followed by a Heck coupling reaction, a Mitsunobu reaction and a final intramolecular cycloaddition reaction thereby leading to the isolation of the expected heterocyclic compounds with an overall yield of up to 69 %. In addition, the chirality introduced in the intermolecular C(sp3)–H amination reaction allows controlling the configuration of the three other stereocenters created in the intramolecular cycloaddition reaction. A second sequence starts from benzocyclobutene and affords fused benzo-octahydroindole derivatives over three steps.