Regio- and Stereoselective Synthesis of 1-/3-Sulfone Sugars Controlled by the Amount of SnCl <sub>4</sub>
A SnCl<sub>4</sub>-mediated regioselective sulfonylation of glycal donors with sulfinic acids enables stereodivergent synthesis of 1-sulfone sugars (0-10 mol % SnCl<sub>4</sub>) or 3-sulfone sugars (1 equiv of SnCl<sub>4</sub>), respectively. Mechanistic studies reveal that sulfinic acid can activate the C3 leaving group alone to form sulfone glycosides, while excess SnCl<sub>4</sub> promotes the 1,3-shift to afford 3-sulfone sugars. The protocol exhibits broad substrate scope, including late-stage modification of natural products, with excellent regio-/stereoselectivity.
Authors
- Nengzhong Wang (ORCID: https://orcid.org/0000-0003-1690-7611)
- Yimin Xiang
- Linxuan Li (ORCID: https://orcid.org/0000-0001-9836-1442)
- Tao Xiong
- Hui Yao
- Jing Xu
- Nianyu Huang
Institutions
- China Three Gorges University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-21
- DOI
- https://doi.org/10.1021/acs.orglett.5c05313
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00