Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams (Beilstein Journal of Organic Chemistry)

Abstract Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz’s reagent-mediated reductive amide functionalization followed by a variant of the Ugi–azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title products. Finally, some surprising observations regarding the mechanism of their formation were made. Beilstein J. Org. Chem. 2021, 17, 115–123. doi:10.3762/bjoc.17.12