To access N-heterocycles substituted at the α-position to the nitrogen, retrosynthetic analysis would suggest this methodology may be extended to diol substrates containing a secondary alcohol, to retain or generate a stereocentre. Although this has been demonstrated asymmetrically, the scope remains limited to few examples solely employing benzylamines, due to poor chemoselectivity often affording diamine products through multiple intermolecular amination reactions. Therefore, additional deprotection and alkylation steps are required to access a wider range of products. While intramolecular hydroamination offers an alternative route to these scaffolds through cyclisation, much of the recent research has focused on C-H substitution at this position. Traditionally, this transformation has been performed using low temperature lithiation chemistry, but more modern methods have achieved it under preferable conditions by utilizing transition metal and photoredox catalysis. Although synthesis of di-α-substituted heterocycles has been achieved through the double reductive amination of diketone compounds, with key examples described in total and iminosugar syntheses, no general asymmetric catalytic platform has yet been demonstrated. Instead, strategies that prioritise redox neutral cyclisation chemistry (i.e. Paal-Knorr) followed by a global reduction are often preferred, despite the challenges in stereo-control afforded by the simultaneous generation of multiple stereocentres.