Stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis

Herein, we reported the stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis and found a suitable system to resolve many challenges, such as the tolerance towards the density of functional groups, the variability of the anomeric position, the compatibility of appropriate catalyst combinations, the regioselectivity of nucleophiles, and the match/mismatch problems between chiral substrates and chiral ligand-metal complexes. The method enables the efficient preparation of a series of unnatural C-glycosamino acid skeletons bearing two contiguous stereogenic centers in good yields with excellent diastereos-electivity. From this crucial precursor, various C-glycosamino acid derivatives have been achieved diversely. The readily prepared C-glycosamino acid hybrids will meet the growing demands for the development of new molecular entities for discovering new drugs and materials. This stereodivergent synthesis of C-glycosamino acids will further accelerate the study of their structural features, mode of action, and potential biological applications in the near future.