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

Abhijit Sau, M. Carmen Galan*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

27 Citations (Scopus)
265 Downloads (Pure)

Abstract

Pd(MeCN)2Cl2 enables the alpha-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to pre-activate either donor or nucleophile. Mechanistic studies sug-gest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium inter-mediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with the syn-thesis of a range of glycosides and glycoconjugates of synthetic utility.
Original languageEnglish
Pages (from-to)2857-2860
Number of pages4
JournalOrganic Letters
Volume19
Issue number11
Early online date12 May 2017
DOIs
Publication statusPublished - 2 Jun 2017

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