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 multi-component 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.
Keywords: amide functionalization; iminosugars; Schwartz’s reagent; tetrazole
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Więcław, M. M.; Furman, B. Beilstein Arch. 2020, 2020118. doi:10.3762/bxiv.2020.118.v1
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