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

A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the...

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Bibliographic Details
Published in:Organic letters 2018-04, Vol.20 (7), p.1936-1940
Main Authors: Yi, Duk, Zhu, Feng, Walczak, Maciej A
Format: Article
Language:English
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Summary:A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the presence of a bulky phosphine ligand that suppresses the undesired β-elimination. The utility of this reaction has been demonstrated in the preparation of a series of C-glycosides derived from common saccharides resulting in exclusive transfer of anomeric configuration from the anomeric nucleophile to the product, and in the synthesis of empagliflozin, a commercial antidiabetic drug.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00475