We reported a nickel-catalyzed pyridine-forming enantioselective hetero [2+2+2] cycloaddition as a unified approach for constructing chiral carbon-, boron-, and germaniumcentered spiro-skeletons. The required remote stereocontrol is achieved by a designed chiral bulky NHC-Ni(0)-styrene complex. An electron-poor aryl group as chiral sidearm provides a strong π-π stacking with the ligand backbone creates a well-defined C2-symmetric chiral pocket which proved to be pivotal for the induced selectivity of the catalyst. The reaction proceeds via a heterocoupling mechanism with the migratory insertion of an enantiotopic alkyne towards the metallaazirene species being the enantiodetermining step. Moreover, the technology is suitable for rapidly assemble highly complex compounds with attractive and exploitable photophysical and chiro-optical properties. The outlined method considerably enlarges the toolbox to assemble chiral functional materials and to construct boron and germanium heteroatom chirality.