Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides

作者:Lai Mengnan; Wang Qiuyuan; Hua Min; Huang Nianyu*; Yao Hui*
来源:CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42(6): 1694-1705.
DOI:10.6023/cjoc202202002

摘要

An open-air stereoselective preparation of C-aryl fucosides and arabinosides was reported using 3,4-O-carbonate glycals and arylboronicic acids based on a palladium-catalyzed decarboxylative allylation at ambient conditions and the configurations of products were determined by NMR, HRMS and X-ray single crystal diffraction analysis. Competitive reactions indicated that this approach has good compatibility with amino and alcoholic/phenolic hydroxyl groups. Further functionlization of unsaturated C-glycosides can be used to prepare a variety of C-glycosides. This mild method is simple in operation, wide application in substrate range, which provides a new idea for the rapid construction of carbohydrate library.