Design and sterospecific synthesis of modular ligands based upon cis-1,3-trans-5-substituted cyclohexanes

Abstract

A range of eight novel ligands, based on the cis-1,3-trans-5-substituted cyclohexane framework, have been synthesized by a stereospecific route starting from cis-1,3,5-cyclohexanetriol. This route depends on the use of efficient mono-silylation and mono-tosylation procedures, is well optimised, and due to isolation of the diazido alcohol precursor cis-3,5-diazido-trans-hydroxycyclohexane readily allows the synthesis of a sizeable family of related ligands via O-derivatisation. Such derivatisations allow systematic changes between various coordinating, hydrogen bonding and lipophilic groups, allowing potential for this ligand system to be utilised in supramolecular coordination chemistry.