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- Title
Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger's Base Derivatives: Part II.
- Authors
Benkhäuser-Schunk, Christian; Wezisla, Boris; Urbahn, Kirstin; Kiehne, Ulf; Daniels, Jörg; Schnakenburg, Gregor; Neese, Frank; Lützen, Arne
- 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.
- Subjects
HIGH performance liquid chromatography; CRYSTAL structure; CIRCULAR dichroism; DICHROISM; MAGNETIC circular dichroism; VIBRATIONAL circular dichroism; TROGER'S base
- Publication
ChemPlusChem, 2012, Vol 77, Issue 5, p396
- ISSN
2192-6506
- Publication type
Article
- DOI
10.1002/cplu.201200029