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Gold(I)-Catalyzed Access to 1-Alkynyl C-Glycosides from 1-Silylated Alkynes: An Alternative Paradigm for the Direct and α-Stereoselective Alkynylation of Glycosides

Year: 2024

Type: article

Abstract: Analogous to O -glycosides, C -glycosides are natural products exhibiting various bioactivities. Alkynyl C -glycosides represent important key intermediates toward more complex derivatives; however, a convenient access through a single catalytic and highly stereocontrolled step remains an important and only partially solved challenge. Here, a mechanistically designed gold(I)-catalyzed silyl-assisted efficient and highly α-stereoselective process is reported. The postulated mechanism has been ascertained by combining 1 H, 31 P and VT NMR and in situ MS experiments.

Source: ACS Catalysis

DOI: 10.1021/acscatal.4c04293

Authors: Eliot Starck, Mathieu Pascaretti, Catherine Taillier, Aurélien Blanc, Vincent Dalla, Patrick Pale, Jean-Marc Weibel

Institutions: Centre National de la Recherche Scientifique, Institut de Chimie de Strasbourg, Université de Strasbourg, Université Le Havre Normandie, Unité de Recherche en Chimie Organique et Macromoléculaire

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Université de Strasbourg, Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche, Centre National de la Recherche Scientifique, Conseil régional du Grand Est, Région Normandie

OpenAlex ID: W4402740149

FWCI: 0.424

Cites: 62

Cited by: 3

Related to: 10