化学
糖基
芳基
另一个
糖基化
立体选择性
组合化学
亲核细胞
电泳剂
化学选择性
糖基供体
催化作用
立体化学
有机化学
生物化学
烷基
作者
Quanquan Wang,Boon Chong Lee,NingXi Song,Ming Joo Koh
标识
DOI:10.1002/anie.202301081
摘要
Stereoselective C-glycosylation reactions are increasingly gaining attention in carbohydrate chemistry because they enable glycosyl precursors, readily accessible as anomeric mixtures, to converge to a single diastereomeric product. However, controlling the stereochemical outcome through transition-metal catalysis remains challenging, and methods that leverage bench-stable heteroaryl glycosyl sulfone donors to facilitate glycosylation are rare. Herein, we show two complementary nonprecious metal catalytic systems, based on iron or nickel, which are capable of promoting efficient C-C coupling between heteroaryl glycosyl sulfones and aromatic nucleophiles or electrophiles through distinct mechanisms and modes of activation. Diverse C-aryl glycosides were secured with excellent selectivity, scope, and functional-group compatibility, and reliable access to both α and β isomers was possible for key sugar residues.
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