Ir(I)‐Catalyzed C−H Glycosylation for Synthesis of 2‐Indolyl‐C‐Deoxyglycosides

The construction of 2‐deoxy‐C‐glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2‐indolyl‐C‐deoxyglycosides via Ir(I)‐catalyzed, pyridine‐grou...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-11, Vol.363 (21), p.4926-4931
Main Authors: Yu, Changyue, Liu, Yichu, Xie, Xiong, Hu, Shulei, Zhang, Shurui, Zeng, Mingjie, Zhang, Dan, Wang, Jiang, Liu, Hong
Format: Article
Language:English
Subjects:
2-indolyl-C-deoxyglycosides
C-glycosides
Carbohydrates
Chemical synthesis
C−H glycosylation
Functional groups
Indoles
Ir(I)-catalyzed
Stereoselectivity
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Summary:The construction of 2‐deoxy‐C‐glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2‐indolyl‐C‐deoxyglycosides via Ir(I)‐catalyzed, pyridine‐group‐directed C−H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β‐configuration products. Gram‐scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100855