American Chemical Society
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Stereoselective O‑Glycosylation of Glycals with Arylboronic Acids Using Air as the Oxygen Source

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journal contribution
posted on 2022-01-26, 14:06 authored by Qiuyuan Wang, Mengnan Lai, Huajun Luo, Keke Ren, Jingrui Wang, Nianyu Huang, Zhangshuang Deng, Kun Zou, Hui Yao
An open-air palladium-catalyzed O-glycosylation was developed using glycals and arylboronic acids with base additives at ambient conditions. The novel approach enabled facile access to various O-glycosides in high yields, with exclusive 1,4-cis-stereoselectivity tolerating reactive hydroxyl/amino groups. Mechanistic studies indicated that chemo-/stereoselectivity arose from the coordination between palladium and phenols generated in situ by oxidizing arylboronic acids, followed by an intramolecular attack. Isotope-labeling experiments revealed that the oxygen of O-glycosidic bonds came from O2.