α,β‐Unsaturated 2‐Ketoglycosides via Pd‐Catalyzed Carbonylative Heck Reaction of 2‐Iodoglycals
Mariana P. Darbem, Henrique Esteves, Isadora M. de Oliveira, Hélio A. Stefani
Abstract
The synthesis of C ‐glycosides is of great importance in the field of carbohydrate chemistry given its ubiquity in biologically active molecules. Herein, we describe a protocol for the Pd‐catalyzed carbonylative Heck reaction of activated olefins and 2‐iodoglycals. A variety of α,β‐unsaturated 2‐ketoglycosides were obtained in up to 89 % yield using d ‐glucal, d ‐galactal, d ‐xylal, and l ‐arabinal derivatives.
Topics & Concepts
ChemistryHeck reactionCatalysisGlucalYield (engineering)Organic chemistryPalladiumCombinatorial chemistryMetallurgyMaterials scienceCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchSynthesis of Organic Compounds