Seven racemic derivatives of Tröger’s base—the 1,7‐dibromo‐substituted derivative 3, the 2,8‐dibromo‐substituted derivative 4, the 2,8‐diiodo‐substituted derivative 5, the 3,9‐diiodo‐substituted derivative 6, the 4,10‐dibromo‐substituted derivative 7, its singly debrominated analogue 8, and the 2,8‐diamino‐substituted derivative 9 in its Fmoc‐protected form—were synthesized and successfully resolved by (recycling) HPLC on a stationary Whelk‐O1 phase at a semipreparative scale. These are valuable functionalized C2‐symmetric building blocks for further applications. Their absolute configurations were determined by X‐ray crystal structure analysis and/or by comparison of their quantum chemically calculated circular dichroism and UV/Vis spectra with the experimental obtained spectra.