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

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Neese,  Frank
Research Department Neese, Max Planck Institute for Bioinorganic Chemistry, Max Planck Society;

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Citation

Benkhäuser-Schunk, C., Wezisla, B., Urbahn, K., Kiehne, U., Daniels, J., Schnakenburg, G., et al. (2012). Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II. ChemPlusChem, 77(5), 396-403. doi:10.1002/cplu.201200029.


Cite as: http://hdl.handle.net/21.11116/0000-0007-E4FB-D
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.