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A stereoselective organocatalyzed C-glycosylation of indole: implications of acceptor–catalyst–donor interactions
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-07 , DOI: 10.1039/d4qo01873g
Lihuang Xie, Wenchao Liu, Zhenbo Guo, Qinbo Jiao, Xiaomin Shen, Tianfei Liu, Chunfa Xu

A stereoselective pyridinium hexafluorophosphate-catalyzed C-glycosylation of indole is presented, featuring the plausible formation of a catalyst–acceptor complex and a crucial H-bond between the N–H group of indole and the oxygen atom at the C6 position of the glycosyl donor, which are proposed to collectively facilitate the glycosylation process. This reaction proceeds under mild conditions, enabling the selective synthesis of a wide range of C-indolyl glycosides.

中文翻译:


吲哚的立体选择性有机催化 C-糖基化:受体-催化剂-供体相互作用的影响



提出了一种立体选择性六氟磷酸吡啶催化的吲哚 C-糖基化反应,其特点是催化剂-受体复合物的合理形成以及吲哚的 N-H 基团与糖基供体 C6 位置的氧原子之间的关键 H 键,这被提出共同促进糖基化过程。该反应在温和的条件下进行,能够选择性合成多种 C-吲哚基糖苷。
更新日期:2024-11-07
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