Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides

Wang C, Krupp A, Strohmann C, Grabe B, Loh CCJ (2024) J Am Chem Soc.

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In view of the uprising development of chalcogen bonding (ChB) catalysis in stereoselective carbohydrate synthesis, the Loh research group reported lately in JACS that the scarcely investigated iminoglycosylation can be robustly catalyzed by a phosphonochalcogenide catalyst to access highly demanded α-iminoglycosides or aza-sugars using mild conditions. Aza-sugars are glycomimetics that are endowed with a broad biological activity profile and possess relevance in a multitude of diseases.

Through meticulous experimental and computational investigations, a novel reaction manifold based on iterative ChB catalyst-substrate engagements and disengagements in multiple elementary steps was unraveled.