Gold-Catalyzed Intramolecular Coupling Reduction for Direct Synthesis of Indole-Fused Iminosugars
In the presence of Hantzsch ester and with JohnPhosAuCl/AgOMs as catalysts, a series of indole-fused iminosugars were obtained in good yields by the intramolecular reductive coupling reaction of iminosugar <i>C</i>-glycoside, in which the terminal alkyne could be coupled with indole and further reduced to methyl. The substrates of iminosugar <i>C</i>-glycosides were conveniently prepared by a three-component reaction of tosylated/mesylated sugar, propargylamine, and indole derivatives. The advantages of this protocol are its simplicity and efficiency in constructing the complex indole-fused iminosugars.
Authors
- Jilai Wu (ORCID: https://orcid.org/0000-0002-8236-0709)
- Likai Zhou
- Chao Wei (ORCID: https://orcid.org/0000-0002-7425-5132)
- Yuhui Liu (ORCID: https://orcid.org/0000-0001-8873-5834)
- Hua Chen (ORCID: https://orcid.org/0000-0001-5564-4610)
- Xiaoyan Huang (ORCID: https://orcid.org/0000-0001-7322-2796)
- Weilin Yang
- Lijing Feng
Institutions
- Comprehensive Clinical Research (US)
- Hebei University (CN)
- Xingtai University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-14
- DOI
- https://doi.org/10.1021/acs.joc.5c00593
- Citations
- 2
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- National Natural Science Foundation of China
- Department of Education of Hebei Province
- Natural Science Foundation of Hebei Province
- Hebei University