AuCl <sub>3</sub> – <i>t</i> BuCN Catalysis in 1,2- <i>trans</i> 2-Deoxy-2-fluoro Glycosidic Bond Formation
Herein we report a general and efficient AuCl<sub>3</sub>-<i>t</i>BuCN cooperative catalysis system for the synthesis of 1,2-<i>trans</i> 2-deoxy-2-fluoro-glycosides. The reaction proceeds rapidly (15 min) under mild conditions, affording high stereoselectivity across a broad range of glycosyl donors and acceptors (40 examples, up to quantitative yield), thus enabling the streamlined chemoenzymatic assembly of fluorinated analogues of human milk oligosaccharides (HMOs). The current work provides a practical solution to long-standing challenges in the stereoselective construction of fluorinated carbohydrates.
Authors
- Richard R. Schmidt (ORCID: https://orcid.org/0000-0001-6398-9053)
- Zhentao Zhang
- Tong Li (ORCID: https://orcid.org/0000-0002-2341-3372)
- Xing Chen (ORCID: https://orcid.org/0000-0002-1396-3100)
- Yuanyuan Li (ORCID: https://orcid.org/0000-0003-2155-0901)
- Tianlu Li (ORCID: https://orcid.org/0000-0002-0674-3687)
- Peng Peng (ORCID: https://orcid.org/0000-0003-4625-6610)
Institutions
- Shenzhen University (CN)
- University of Konstanz (DE)
- Zhengzhou University (CN)
- Carbohydrate Competence Center (NL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-08
- DOI
- https://doi.org/10.1021/acs.orglett.5c04361
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00