Concave macrocycles have gained significant interest as potential platforms for use in an array of host-guest applications. Cyclodextrins are cavitary compounds that are highly attractive for supramolecular design since they are naturally occurring, and can be solubilized in water or organic solvents, depending on their protective groups. Due to their symmetrical cavity however (n glucose units), selectively functionalizing them is difficult to achieve. By use of selective debenzylation, we propose a successful method by which it is possible to introduce a chiral spatial arrangement on the primary rim to then facilitate its selective modification. Herein, we present an efficient synthetic pathway to yield two enantiomeric spatial arrangement s of primary alcohols that have potential to be used as ligands in metal-catalysis, enzyme mimics, and for improvement in the discrimination ability of chiral HPLC.

Selective functionalization of the primary rim of alpha-cyclodextrin for practical applications

255th National Meeting (2018)

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