Jaiswal Manoj K, Gupta Abhishek, Yadav Mangal S, Pandey Vinay K, Tiwari Vinod K
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India.
Chemistry. 2023 Oct 2;29(55):e202301749. doi: 10.1002/chem.202301749. Epub 2023 Sep 1.
A novel organocatalyzed [3+2] cycloaddition reaction of nitroolefins with glycosyl azides as well as organic azides has been developed for successful construction of 1,5-disubstituted triazolyl glycoconjugates. This metal-free and acid-free, regioselective synthetic protocol proceeds in the presence of only Schreiner thiourea organocatalysts, which enable the required activation of nitroolefins through double hydrogen bonding. The straightforward, operationally simple, and regioselectivity of this methodology, complementing to the classical RuAAC catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles. In the presence of catalytic amount of Schreiner thiourea organocatalyst, organic azides react with a broad array of nitroolefins producing a series of diverse 1,5-disubstituted 1,2,3- triazoles in good yields with excellent regioselectivity.
已开发出一种新型的有机催化硝基烯烃与糖基叠氮化物以及有机叠氮化物的[3+2]环加成反应，用于成功构建1,5-二取代的三唑基糖缀合物。这种无金属、无酸的区域选择性合成方案仅在施赖纳硫脲有机催化剂存在下进行，该催化剂通过双氢键实现硝基烯烃所需的活化。该方法直接、操作简单且具有区域选择性，是对经典的钌催化的1,5-二取代1,2,3-三唑合成的补充。在催化量的施赖纳硫脲有机催化剂存在下，有机叠氮化物与多种硝基烯烃反应，以良好的产率和优异的区域选择性生成一系列多样的1,5-二取代1,2,3-三唑。
