Iminosugars constitute one of the most promising classes of glycomimetics as therapeutic agents with several compounds on the market. To improve their glycosidase inhibitory potential, their chemical modulation has been achieved on the endocyclic nitrogen and C-1 position but the lack of innovative synthetic strategies has limited structural diversity. Increasing chemical space is key not only to improve their biological/physico-chemical properties but also to identify new biological activities. The chemical modulation of the C2 position has been poorly scrutinized despite recent encouraging data. Investigating these two positions further is the goal of this project that requires both suitable precursors and innovative methods to rapidly introduce structural diversity in a regio- and stereoselective manner. High structural diversity has been introduced in glycosides thanks to glycals, a subclass of unsaturated monosaccharides. Their metal-assisted functionalization not only allowed their late-stage functionalization at C1 and C2 but also in a stepwise manner at C2 then at C1. We have recently developed several metal-catalyzed methodologies exploiting 2-iodoglycals for the functionalization at C2 position but also for the C1-H functionalization of C2-amidoglycals. Iminoglycals, nitrogen counterparts of glycals, are underexploited synthons and perfect precursors for our purpose and we have been able to functionalize the C2 position under metal-catalyzed conditions starting from an unprecedented 2-iodoiminoglycal. By combining our expertises in glycomimetics and metal-catalyzed functionalization supported by DFT calculations to anticipate the reactivity of these molecules, we plan to unlock the chemistry of iminoglycals to significantly increase the chemical space of iminosugars through chemical modulation of their C1 and C2 positions, a work that should lead to new glycomimetics with biological/therapeutic potential.