Dearomatization reactions are widely recognized as powerful methods for the synthesis of highly functionalized three-dimensional structures from simple planar aromatic compounds. Among those, catalytic asymmetric dearomatization (CADA) reactions are very attractive due to the abundance and ready availability of aromatic compounds and the direct access to enantiopure polycycles and spirocycles offered by them. That latter are frequently the key motifs in biologically active natural products and pharmaceuticals. However, due to the extra stability of “aromaticity” of the arenes, their dearomatization reactions with good enantioselective control has been a great challenge. In this talk, we present our recent results toward the development of catalytic asymmetric dearomatization reactions. The dearomatization reactions of indoles, pyrroles, phenols, naphthols, and pyridines have been achieved, affording various highly functionalized heterocycles bearing all-carbon quaternary chiral centers in most of the cases. These results provide not only the efficient synthesis of highly enantioenriched spiro- or polycycles, but also a novel concept in asymmetric catalysis.