Synthesis of spiroaminal 2,8-disubstituted-1,7-diazaspiro[5,5]undecane derivatives

(N,N)-spiroaminal is an interesting chemical motif yet it is neglected in synthetic research compared to its analogues (O,O)-spiroketal and (O,N)-spirohemiaminal. The Barrett group recently reported synthetic methods for (N,N)-spiroaminals: 1,7- diazaspiro[5,5]undecane (I) and tetrahydrospirobiquinolines (II). i,ii This research focuses on the development of synthetic methods for (N,N)- spiroaminals and investigation of their applications. The first part of this thesis consists of synthetic methods for 2,8-disubstituted-1,7-diazaspiro[5,5]undecane (III). The key synthetic step involves bi-directional Horner–Wadsworth–Emmons olefination of chiral aldehydes (IV) with diphosphate (V). iii The second part of this thesis focuses on the development attempts to synthesise chiral ligands with spiroaminal backbone, including di-amide, di-phosphine, phosphite, bis(oxazoline) and macrocyclic ligands. 4 The final part of this work concentrates on the coordination chemistry study of the newly synthesised spiroaminal compounds with a range of metal sources.Open Acces