钯
糖基化
糖基
芳基
糖苷
氧代碳
亲核细胞
化学
立体选择性
立体化学
组合化学
催化作用
有机化学
生物化学
烷基
作者
Quanquan Wang,Shuang An,Zhiqiang Deng,Wanjun Zhu,Zeyi Huang,Gang He,Gong Chen
出处
期刊:Nature Catalysis
[Springer Nature]
日期:2019-08-05
卷期号:2 (9): 793-800
被引量:116
标识
DOI:10.1038/s41929-019-0324-5
摘要
C-aryl glycosides are widely found in nature and play important roles in drug design. Despite the significant progress made over the past few decades, efficient and stereoselective synthesis of complex C-aryl glycosides remains challenging, lagging far behind the state of the art of the synthesis of O- or N-glycosides. Here, we report a simple and powerful bioinspired strategy for the stereoselective synthesis of C-aryl glycosides via palladium-catalysed ortho-directed C(sp2)−H functionalization of arenes and heteroarenes with easily accessible glycosyl chloride donors. The catalytic palladacycle intermediate generated via C−H palladation provides a soft aryl nucleophile that can react with glycosyl oxocarbenium ion partners with high efficiency and excellent stereocontrol. The method can be applied to a wide range of arene and heteroarene substrates, glycosyl chloride donors and auxiliary groups. It can simplify the synthesis of a variety of complex C-aryl glycosides and offers a tool for late-stage modification of drug molecules. C-aryl glycosides are present in many natural products and of interest in drug design, but their chemical synthesis is challenging. This work reports an efficient and diastereoselective ortho-directed C−H glycosylation of arenes and heteroarenes with glycosyl chloride using a palladium catalyst.
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