Highly Stereoselective Synthesis of β-Glycosyl Esters via N -Heterocyclic Carbene Catalysis under Aerobic Conditions
Abstract
-heterocyclic carbene (NHC)-catalyzed glycosylation method employing glycosyl bromides as donors and aldehydes as acceptors, which enables facile access to structurally diverse β-glycosyl esters with high yields and excellent stereocontrol. This transformation proceeds under mild, metal-free, and open-air conditions and exhibits broad substrate scope with respect to both reaction partners (54 examples). Notably, the reaction displays broad functional-group compatibility and tolerates nucleophilic hydroxyl groups. Its synthetic utility is illustrated by the late-stage modification of bioactive molecules and a series of synthetic transformations. Overall, our method provides an efficient alternative for the synthesis of valuable β-glycosyl esters.
Fields of Study & Subjects
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Carbohydrate Chemistry and Synthesis
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 29
- Pages
- 9499–9504
- Publication date
- 15 July 2026
- Language
- EN