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

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 op...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-07, Vol.2013 (21), p.4523-4532
Main Authors: Meyer-Eppler, Georg, Vogelsang, Elisabeth, Benkhäuser, Christian, Schneider, Andreas, Schnakenburg, Gregor, Lützen, Arne
Format: Article
Language:English
Subjects:
Chiral resolu­tion
Chirality
Configuration determination
Crystal structure
Cyclophanes
Liquid chromatography
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Summary: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 C2‐symmetric building blocks for the formation of more sophisticated V‐shaped, chiral molecular architectures, as demonstrated by some exploratory transformations. Dissymmetric 4,12‐difunctionalized [2.2]paracyclophane derivatives were prepared and resolved on a semipreparative scale either by conventional or recycling HPLC with a chiral stationary phase. The absolute configurations of the resolved enantiomers were assigned by X‐ray diffraction and/or comparison of specific optical rotations with literature data.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300412