Final Report Summary - SUPRAMOLORGANOCAT (Applications of organocatalysis to supramolecular chemistry) The development of new synthetic strategies that allow increasingly rapid access to structural complexity and new molecular architectures remains one of the fundamental challenges for the chemical sciences. Over the last ten years, organocatalysis - particularly that associated with chiral secondary amines - has become an established and powerful synthetic tool for the chemo- and enantioselective functionalisation of carbonyl compounds, and has already had significant impact in the synthesis of natural products, intermediates for pharmaceuticals and other structurally complex biologically active compounds. The aim of this project was to develop and investigate for the first time the application of organocatalytic chemistry to complex structure synthesis in supramolecular chemistry. In particular, I intend to investigate the utility of these reactions in facilitating the first organocatalytic 'active template' synthesis of rotaxanes. The development of synthetic routes towards macrocyclic analogues of imidazolidinone, proline and prolinol ether organocatalysts was undertaken - promising results in the synthesis of the proline macrocycle were achieved. Several reaction conditions and reactants were screened to effect rotaxane formation via proline-macrocyle-mediated organocatalysis; however, early attempts were unsuccessful. Latterly, efforts were directed at modifications to the design of the macrocycle, to improve the reactivity of the macrocyclic organocatalyst.
