A key challenge in the development of a unified strategy for the construction of carbon, boron, and germanium-centered spirocyclic skeletons lies in the identification of a method of stereocontrol tolerant to distinctive tetrahedral geometries of the spirocyclic center and to diverse functionalities. A remote desymmetrizing ring closure appeared to us as promising strategy to construct the targeted chiral spirocycles. Such approach involves introducing an enantiotopic bis-substitution on the carbon, boron, and germanium-based cyclic substrates. The enantioselective ring closure involving both enantiotopic substituents selectively create the spiro stereogenic center at a remote position (Fig ). Examples for such strategies for the asymmetric construction of spirocycles are rare and exhibit largely limited scope. We looked to transition-metal-catalyzed [2+2+2] cycloadditions as exploitable strategy for the desymmetrizing ring closure via arene formation. Integrating chiral spiro-skeletons formation with the formation of a pyridine from two alkynes and a nitrile bears significant value. The pyridine motif substantially enhances utility by an involvement of this group in downstream applications in ligand or material design. Therefore, we considered an enantioselective hetero [2+2+2] cycloaddition of two distal enantiotopic bis-alkynes with a nitrile as a promising strategy for constructing chiral spiro-skeletons if three key challenges could be addressed (Fig ). Firstly, the different side reactions of the bis-alkyne substrates such as alkyne cyclotrimerization or oligomerization needs to be suppressed. Secondly, since the stereo-differencing element is remote from the hetero [2+2+2] cycloaddition reaction site, a chiral catalyst with the ability for efficient enantio-discrimination between the distal enantiotopic alkynes is required. Thirdly, the catalyst needs to accommodate the distorted and enlarged geometries of the boron and germanium centers as well as work under mild reaction conditions to ensure survivability of these more fragile bonds. Leveraging our experience in designing and applying chiral NHCs in asymmetric catalysis, we prepared a C2-symmetric chiral Ni(0)NHC styrene complexes able to selectively catalyze hetero [2+2+2] cycloadditions assembling carbon-, boron-and germanium-centered spirocyclic skeletons via a long-range enantioinductions. Mechanistic insights point towards a heterocoupling mechanism and allow for insight into the enantiodetermining step. Moreover, the rapid assembly of complex chiral compounds with attractive photophysical and chiroptical properties underscore the applicability for functional materials. To gain a better understanding of how steric and electronic modulation in nickel-NHC complex influence enantioselectivity, we analyzed the crystal structures of Ni1, Ni2, and Ni3. The chiral-side arm of Ni1 complex is relatively flexible. Compared to Ni2 and Ni3, it has a different chiral pocket and less buried volume. However, we observed no substantial visual differences in the chiral pockets of Ni2 and Ni3. Furthermore, attempts to improve the design of Ni2, an incorporation of 3,5-dimethyl substituents to enhance the steric bulk of the chiral side arm resulted in a substantial drop yield, without improvement in enantioselectivity (Table ). Thus, it became evident that simply a more confined microenvironment is unlikely to improve selectivity. Regarding electronic effects, weak π-π stacking was observed between the chiral side arm and the acenaphthylene motif in Ni2 complex (Fig. ), reducing the flexibility of the chiral sidearm. In total, 6 different molecules of Ni2 complex appear in the unit cell of the crystal (Fig. ). These variations at the distance between the chiral sidearms and the acenaphthylene backbone, indicating that the flexibility of the chiral side arms might be still relevant (Fig. ). The electron density of the chiral sidearm in Ni3 complex was effectively reduced by the introduction of 3,5-difluoro substituents. This modulation resulted in stronger π-π stacking with the acenaphthylene backbone establishing a more defined chiral environment as depicted in the crystal structure of Ni3 (Fig. ). These findings underscore that a chiral sidearm displaying rigidity and stability to the C2 symmetric chiral environment is of strong relevance for achieving high levels of enantioinduction. Detailed reaction condition optimizations are available in Table -S8.