Open-Air Stereoselective Construction of <i>C</i>-Aryl Glycosides
Mengnan Lai, Karwan Abdulmajed Othman, Hui Yao, Qiuyuan Wang, Yongkui Feng, Nianyu Huang, Ming‐Guo Liu, Kun Zou
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.
Topics & Concepts
ChemistryStereoselectivityDecarboxylationSteric effectsArylGlycosylationSelectivityGlycosideSubstrate (aquarium)PalladiumOrganic chemistryCatalysisAlkylOceanographyBiochemistryGeologyCarbohydrate Chemistry and SynthesisChemical Synthesis and AnalysisSynthetic Organic Chemistry Methods