Is potential coordination of alkali metal ions to stereodefined polyoxygenated cyclohexanes an adequate driving force for fostering the adoption of axial conformers?

Abstract

Inositol orthoesters have been developed as precursors to stereodefined hexakis polyoxygenated cyclohexanes. The objective of the study was to determine if all- trans systems could be coaxed by alkali metal ions into adopting the all- axial coordinative features. This high level coordination cannot be matched by epimers whose only option is to experience monocomplexation. Only very low levels of coordination were exhibited in solution by the ligands in question. Electrospray ionization mass spectrometry was also used to evaluate the metal complexation properties of the inositol ligands based on competition experiments involving each ligand and one or more metals.