Investigations into the distal-functionalisation of the phenols of racemic C 4symmetric tetramethoxyresorcinarene has led to a simple, single-step procedure that allows the isolation of gram quantities of partially silylated derivatives, with the targeted distally-silylated resorcinarene being obtained in a yield of 31%. These partially-silylated derivatives would serve as versatile intermediates for the selective functionalisation of this elegant architecture. The solid state structures of many of these derivatives have been determined by single crystal X-ray crystallography.
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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