1621188-47-3Relevant articles and documents
Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
Palo-Nieto, Carlos,Sau, Abhijit,Galan, M. Carmen
, p. 14041 - 14044 (2017)
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.
Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
Sau, Abhijit,Williams, Ryan,Palo-Nieto, Carlos,Franconetti, Antonio,Medina, Sandra,Galan, M. Carmen
supporting information, p. 3640 - 3644 (2017/03/21)
Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.