ACS Catalys [COSyS]

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 ¹H, ³¹P and VT NMR and in situ MS experiments.

Graphical Abstract:

Reference:

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

E. Starck, M. Pascaretti, C. Taillier, A. Blanc, V. Dalla, P. Pale, and J.-M. Weibel

ACS Catal. 2024, 14, 19, 14863–14870, DOI : https://pubs.acs.org/doi/10.1021/acscatal.4c04293

 

Contacts:

J.-M. Weibel, A. Blanc and P. Pale,  team COSyS, Institut de Chimie de Strasbourg (UMR 7177).