The synthesis of N-glycosides has received significant attention
due to their crucial role in carbohydrate chemistry. Despite
considerable advancements were developed in the construction of
N-glycosides, methods for the stereoselective construction of
2-deoxy-α-N-glycosides are still limited. Herein, we
disclosed a nickel-catalyzed hydroamination of glycals under mild
conditions. This transformation could allow for the stereoselective
synthesis of an array of 2-deoxy-α-N-glycosides with
excellent α-stereoselectivity. Nickel-catalyzed glycosylation
reactions, particularly those involving anomeric
C(sp3)-metal bond formation, have proven to be an
effective and stereoselective strategy for producing various
N-glycosides. Additionally, with highlight the application of
this reaction, γ-sugar amino acid derivatives were synthesized by one
step. |