The direct functionalization of carbon-hydrogen bonds is an emerging tool to establish more sustainable and efficient synthetic methods. We present its implementation in a cascade reaction that provides a rapid assembly of functionalized indanylamines from simple and readily available starting materials. Careful choice of the ancillary ligand - an electron-rich bidentate phosphine ligand - enables highly diastereoselective rhodium(I)-catalyzed intramol. allylations of unsubstituted ketimines induced by a directed C-H bond activation and allene carbo-metalation sequence.