Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 21, Pages 4523-4532Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300412
Keywords
Cyclophanes; Chiral resolution; Liquid chromatography; Configuration determination; Chirality
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [SFB 624]
- 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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