Open-Air Stereoselective Construction of C-Aryl Glycosides
Mengnan Lai1, Karwan Abdulmajed Othman1,2, Hui Yao1
1Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences , China Three Gorges University , Yichang 443002 , P.R. China.
Abstract:
A new methodology of stereoselective C-glycosylation has been developed with 3,4-O-carbonate glycals and boronic acids, catalyzed by 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate under open-air conditions at room temperature. This mild method is simple in operation, wide in substrate range, and tolerant in alcoholic/phenolic hydroxyl and amino groups. High to excellent yields were observed for all substrates tested, with the driving force mainly contributed by decarboxylation. Meanwhile, the high 1,4-trans-selectivity was achieved by steric effects as proposed.
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