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Stereocontrolled Synthesis of 2‑Deoxy‑C‑glycopyranosyl Arenes Using Glycals and Aromatic Amines

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journal contribution
posted on 08.05.2018, 03:13 by Shengbiao Tang, Qiannan Zheng, De-Cai Xiong, Shende Jiang, Qin Li, Xin-Shan Ye
An efficient and stereoselective one-pot, two-step tandem α-arylation of glycals from readily available aryl amines via stable diazonium salts has been developed. Moreover, the stereoselective preparation of the challenging β-C-glycosyl arenes by the anomerization of α-C-glycosides using HBF4 is also described. This protocol has a broad substrate scope and a wide functional-group tolerance. It can be used for the gram-scale preparation of 3-oxo-C-glycosides, which are versatile substrates for the preparation of many biologically important C-glycosides.