Highly Regio- and Stereoselective Construction of 2-Deoxy-α-glycosylated N -Heterocycles Enabled by Organocatalysis
Abstract
We disclose a metal-free glycosylation method for the efficient and stereospecific synthesis of 2-deoxy-α- N -glycosides, which employs a low-cost pyridinium salt catalyst with readily accessible azole heterocycles and glycals. This organocatalytic approach features a broad substrate scope and high functional group tolerance, affording a diverse array of heterocyclic N -glycosides in high yields with exclusive α-selectivity and N -site selectivity. The underlying mechanism of this glycosylation involving noncovalent interactions between the azole nucleophile and catalyst was elucidated via NMR studies, control experiments, and DFT calculations. Overall, our method provides an efficient, highly α-stereoselective strategy for accessing high-value glycosylated N -heterocycles and will expedite their biological investigations.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Chemical Synthesis and Analysis
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 23
- Pages
- 7496–7502
- Publication date
- 2 June 2026
- Language
- EN