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Keywords:

  • absolute configuration;
  • circular dichroism;
  • enantiomeric resolution;
  • HPLC techniques;
  • quantum chemical calculations;
  • Tröger’s base

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 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.