Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II

Abstract 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 C 2 ‐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.