Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C-Glycosides of Biomedical Relevance

• DOI: 10.1021/acs.orglett.8b00475
• Publication Date: 2018-03-12T13:05:03Z
• Authors: Duk Yi; Feng Zhu; Maciej A. Walczak
• Keywords: Stereospecificity; Coupling reaction

A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis aryl C-glycosides is reported. This process capitalizes on a stereoretentive configurationally stable C1 stannanes and promoted by palladium catalyst presence bulky phosphine ligand that suppresses undesired β-elimination. The utility this has been demonstrated preparation series derived from common saccharides exclusive transfer configuration nucleophile to product, empagliflozin, commercial antidiabetic drug.