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

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.