Details

Autor(en) / Beteiligte

• Zhao, Wei-Cheng
• Li, Rui-Peng
• Ma, Chao
• Liao, Qi-Ying
• Wang, Miao
• He, Zhi-Tao

Titel

Stereoselective gem-C,B-Glycosylation via 1,2-Boronate Migration

Ist Teil von

• Journal of the American Chemical Society, 2022-02, Vol.144 (6), p.2460-2467

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A novel protocol is established for the long-standing challenge of stereoselective geminal bisglycosylations of saccharides. The merger of PPh3 as a traceless glycosidic leaving group and 1,2-boronate migration enables the simultaneous introduction of C–C and C–B bonds at the anomeric stereogenic center of furanoses and pyranoses. The power of this method is showcased by a set of site-selective modifications of glycosylation products for the construction of bioactive conjugates and skeletons. A scarce metal-free 1,1-difunctionalization process of alkenes is also concomitantly demonstrated.