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Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

[Image: see text] Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room...

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Detalles Bibliográficos
Autores principales: Palo-Nieto, Carlos, Sau, Abhijit, Galan, M. Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5951607/
https://www.ncbi.nlm.nih.gov/pubmed/28934850
http://dx.doi.org/10.1021/jacs.7b08898
Descripción
Sumario:[Image: see text] Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles.