(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).
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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.