Synthesis of Distally‐Bridged Chiral Resorcinarene Crowns.
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Our interest in the potential of chiral tetramethoxy-resorcinarene as agents for chiral recognition has led us to synthesise twelve distally-bridged chiral resorcinarene crowns. The fascinating architecture of these partially-enclosed chiral basket molecules is evident in the solid-state structures which have been determined by single crystal X-ray crystallography. Moreover, the enantiomers of these chiral resorcinarene crowns have been resolved via diastereomeric resolution, with the absolute configuration of the diastereomers being determined by X-ray crystallography. This work enables further exploration of these enantio-pure chiral baskets as possible chiral resolving agents.
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McIldowie, Matthew (2007)This study investigates methods for the synthesis and resolution of chiral resorcinarenes.The first direct synthesis of C4 dissymmetric resorcinarenes by the Lewis acid catalysed condensation of 3-alkoxyphenols and alkyl ...
Mcildowie, Matthew; Mocerino, Mauro; Ogden, Mark (2010)Calixarene and resorcinarene macrocycles are renowned for their ability to form inclusion complexes or act as molecular scaffolds. The addition of chirality to these non-planar molecules is an exciting enhancement of their ...
Vaughan, Jamila; Bertata, Munna Ali Mohamed; Skelton, B.W.; Ogden, Mark ; Mocerino, Mauro (2019)The synthesis and characterization of an amide-functionalized axially chiral resorcinarene, 14,36,56,76-tetra-2-oxo-2-(2-hydroxyethylamino)ethoxy-16,34,54,74-tetramethoxy-2,4,6,8- tetrapropylresorcinarene, is reported. ...