4.5 Article

Synthesis, Chiral Resolution, and Absolute Configuration of Dissymmetric 4,12-Difunctionalized [2.2]Paracyclophanes

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 21, Pages 4523-4532

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300412

Keywords

Cyclophanes; Chiral resolution; Liquid chromatography; Configuration determination; Chirality

Funding

  1. Deutsche Forschungsgemeinschaft (DFG) [SFB 624]
  2. Ministry of Innovation, Science, and Research of the State of North Rhine-Westphalia (ENQUETE)

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Racemic 4,12-difunctionalized [2.2]paracyclophanes were synthesized and successfully resolved by (recycling) HPLC on a stationary CHIRALPAK IA phase at a semipreparative scale. Their absolute configurations were determined by X-ray crystal structure analysis and/or by comparison of their specific optical rotations with literature data. These are valuable functionalized C-2-symmetric building blocks for the formation of more sophisticated V-shaped, chiral molecular architectures, as demonstrated by some exploratory transformations.

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