Bicyclo[3.3.1]nonane-2,6-dione and its utilization as a core building block in supramolecular architectures

In this work, the structural framework of bicyclo[3.3.1]nonane has been utilized as a core building block in the synthesis of novel supramolecular architectures. The solid state of variously functionalized derivatives of this bicyclic compound has also been addressed from a supramolecular point of view.
An improved methodology for the large scale preparation of bicyclo[3.3.1]nonane-2,6-dione was developed. Kinetic resolution using Baker’s yeast for sweet dough made it possible to produce large quantities of optically pure bicyclo[3.3.1]nonane-2,6-dione. The kinetic resolution was further improved with genetically engineered yeast. Enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione was then employed in the construction of molecular tweezers and a supramolecular macrocycle that was assembled using non-covalent synthesis.
The crystal structure of eight derivatives of bicyclo[3.3.1]nonane were elucidated and subsequently analysed by means of the structural network approach, with the aim to gain understanding in how the structural features of this class of compounds in combination with weak hydrogen bonds dictate its solid state.