Organic Letters
Organic Letters
5 years ago

Palladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals

Palladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals
Abhijit Sau, M. Carmen Galan
Pd(MeCN)2Cl2 enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to preactivate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with the synthesis of a range of glycosides and glycoconjugates of synthetic utility.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01092

DOI: 10.1021/acs.orglett.7b01092

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