Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

Carlos Palo-Nieto, Abhijit Sau, Robin Jeanneret, Pierre-Adrien Payard, Aude Salamé, Maristela Braga Martins-Teixeira, Ivone Carvalho, Laurence Grimaud, M Carmen Galan

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

Abstract

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

Original languageEnglish
JournalOrganic Letters
Early online date19 Feb 2020
DOIs
Publication statusE-pub ahead of print - 19 Feb 2020

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