NiCl <sub>2</sub> /Hdipm-Catalyzed 2-OH-Selective Alkylation of Glycoside <i>trans</i> -Diols
A strategy for site-selective controllable alkylation of α-glycosides bearing an equatorial <i>trans</i>-2,3-diol utilizing NiCl<sub>2</sub>/Hdipm or SnCl<sub>2</sub>/DIPEA catalysis is reported. Studies on various catalytic systems have revealed that only the NiCl<sub>2</sub>/Hdipm-catalyzed alkylation could achieve excellent 2-O selectivity. This method was further applied to the efficient one-pot synthesis of both 2-OH and 3-OH glycosyl acceptors. Via the one-pot method, 2-<i>O</i>-methyl-empagliflozin (a potential anti-heart failure drug) was synthesized from empagliflozin with a total 76% yield.
Authors
- Lanyue Zhang (ORCID: https://orcid.org/0000-0002-5153-5473)
- Hai Dong (ORCID: https://orcid.org/0000-0002-9794-1805)
- Jian Lyu (ORCID: https://orcid.org/0009-0006-0036-3735)
- Yang‐Fan Guo
- Guohui Zhang (ORCID: https://orcid.org/0000-0001-6400-9854)
Institutions
- Ministry of Education (RO)
- Wuhan No.1 Hospital (CN)
- Huazhong University of Science and Technology (CN)
- Wuhan Institute of Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-12
- DOI
- https://doi.org/10.1021/acs.orglett.5c04886
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00