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

Organic Letters
Abhijit Sau, M Carmen Galan

Abstract

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.

References

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Dec 23, 2016·The Journal of Organic Chemistry·Carlos Palo-NietoM Carmen Galan
Feb 18, 2017·Angewandte Chemie·Abhijit SauM Carmen Galan

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Citations

Mar 13, 2018·Organic & Biomolecular Chemistry·Ramakrishna BandiSrinivasan Chandrasekaran
Jul 12, 2019·Beilstein Journal of Organic Chemistry·Madhu Babu TatinaZaher M A Judeh

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Methods Mentioned

BETA
glycosylation

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