Designing chiral ligands with an axial symmetry higher than C -rotational symmetry is one of the most crucial approaches to improving enantioselectivity in asymmetric synthesis. Herein, C -symmetric chiral cage-shaped phosphites are reported. Their Lewis basicity and chiral environment are precisely controlled by the tethered group. The cage-shaped phosphites successfully worked as chiral ligands in Rh-catalyzed asymmetric conjugate additions, realizing acceptable yields with excellent enantioselectivity, and were used to synthesize a pharmacologically important molecule.