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Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts†
Kumar Bhaskar Pal,Mrinmoy Das,Xue-Wei Liu
Organic & Biomolecular Chemistry Pub Date : 03/11/2020 00:00:00 , DOI:10.1039/D0OB00247J
Abstract

An efficient palladium(II) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including D-glucal, D-galactal, D-allal, L-rhamnal, L-fucal, L-arabinal, D-maltal, and D-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity.

Graphical abstract: Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts
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