Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor–acceptor substituted cyclopropanes

•Carbohydrate fused α-amino-γ-lactams were synthesized stereoselectively.•Carbohydrate fused γ-lactams were synthesized.•An α-amino-γ-lactam was extended to the synthesis of a glucopeptide. α-Amino γ-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused α-amino γ-lactam and γ-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide.