Expanding the importance of chirality and implementation of stereogenic information within complex molecular design has recently reached a new level: design of innovative enantiopure scaffolds bearing multiple chiral elements. In particular, regarding sustainability aspects and straightforward use of relatively simple substrates, the C-H activation strategy offers unique opportunities to assemble complex chiral molecules with unique topologies while controlling two stereoselective events in a single transformation. Herein, the emerging field of asymmetric C-H activation allowing rapid construction of atropisomeric molecules bearing a second chirality element, such as a stereogenic center, vicinal chiral axis or planar chirality, is described. Aiming at in-depth comprehension of such innovative systems, the emphasis is put on the nature of stereodiscriminant steps, allowing the simultaneous control of both chiral elements.