Transition metal-catalyzed asymmetric allylic substitution (AAS) is an extremely powerful and versatile method for the synthesis of enantioenriched compounds. As opposed to Pd-catalysis, Ir-catalyzed AAS reactions enable the synthesis of branched products from unsymmetrical allylic electrophiles. This feature of Ir-catalyzed AAS allows for the use of non-prochiral carbon and heteroatom nucleophiles in reactions with unsymmetrical allylic electrophiles. Consequently, a wide range of nucleophiles have been employed during the past two decades.1 In contrast, structurally related asymmetric allenylic substitution reactions are much less explored, and began to emerge only recently, especially under Ir-catalysis. 2 Our laboratory is particularly interested in unexplored classes of carbon nucleophiles, with a special emphasis on enantioselective C–H allylation and allenylation. To this end, we have developed a number of Ir-catalyzed enantioselective transformations leading to overall C(sp3 )−H and C(sp2 )−H all(en)ylations, 3-8 at times in cooperative combination with organocatalysis. 9 Some of these catalytic enantioselective all(en)ylation reactions and their application will be covered in this talk along with our recent work C(sp)‒H allylation.