Base-Catalyzed Bifunctionalization of Phenacyl Bromide with Glycosyl Thiosulfonates to Access Stereoselective Synthesis of Diverse Glycosylthio β-Keto Sulfones
Abstract
A simple and high-yielding strategy to synthesize glycosylthio β-keto sulfones using easily accessible glycosyl thiosulfonates with phenacyl bromide derivatives under metal-free conditions is developed. This method enables the straightforward formation of two new C–S bonds (C–S and C–SO 2 ) simultaneously. Meanwhile, five different sugar thiosulfonates were well tolerated in this reaction, exhibiting high efficiency and broad applicability (up to 94%, 36 examples). The synthetic process was reliable at the gram-scale, thus demonstrating their efficiency and practicality. In addition, a plausible reaction mechanism underlying this method is proposed.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Carbohydrate Chemistry and Synthesis
Synthesis of heterocyclic compounds
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 5
- Pages
- 2037–2054
- Publication date
- 26 January 2026
- Language
- EN