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Nickelaelectro-Catalyzed Glycosyl-Donor Activation Enabling α- C -Alkenyl Glycoside Assembly

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide C -alkenyl glycosides represent an important class of carbohydrates that includes numerous biologically active compounds. We developed a stereoselective and sustainable strategy using anomeric glycosyl halides as radical precursors for reductive alkenylation. This enables efficient anomeric functionalization with excellent α-selectivity through ligand control. Electrochemical halogen-atom transfer ( e -XAT) activates the glycosyl donors, avoiding stoichiometric metal reductants and expensive photocatalysts. This method shows broad substrate scope, including diverse oligosaccharides, delivering high yields and stereoselectivity.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c03327

Authors: Fabian Hinrichs, Rajeshwaran Purushothaman, Lutz Ackermann

Institutions: University of Göttingen, German Centre for Cardiovascular Research

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Deutsches Zentrum für Herz-Kreislaufforschung, Deutscher Akademischer Austauschdienst, Deutsche Forschungsgemeinschaft, European Research Council