We report an enantio- and diastereodivergent synthesis of enantioenriched fluorenes bearing bis-1,3-nonadjacent stereocenters with broad substrate scope and high enantioselectivity (up to 99% ee) under low catalyst loading (0.1 mol %). The key to the success of this method is the pseudo-diastereodivergent desymmetrization of stereoisomers of meso-epoxides enabled by the same organocatalyst. Furthermore, some of the chiral fluorenes obtained exhibit high fluorescence quantum yields (up to 76.6%), as evidenced by photophysical properties studies.