Więcław Michał Mateusz, Furman Bartłomiej
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Beilstein J Org Chem. 2021 Jan 13;17:115-123. doi: 10.3762/bjoc.17.12. eCollection 2021.
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.
在此，我们通过施瓦茨试剂介导的还原酰胺官能化反应，随后进行乌吉-叠氮多组分反应的变体，从单糖直接不对称合成了四唑官能化的1-脱氧野尻霉素衍生物。通过X射线分析明确证实了两种产物的端基构型。这项工作还描述了标题产物有趣的进一步转化实例。最后，对它们的形成机理进行了一些惊人的观察。
