Synthesis, Resolution, and Absolute Configuration of Difunctionalized Tröger's Base Derivatives

Abstract Two racemic derivatives of Tröger's base, the 2,8‐diboronic acid ester 6 and the 3,9‐dibromo‐substituted derivative 5 , were synthesized and successfully resolved by HPLC on a chiral stationary Whelk‐01 phase on a semipreparative scale, thereby giving rise to both enantiomers in a pure form. These functionalized C 2 ‐symmetric building blocks are valuable precursors for a variety of further applications. Their absolute configurations were determined by comparison of their quantum chemically calculated CD and UV/Vis spectra with the experimental ones and were independently confirmed by X‐ray diffraction analysis.