In(OTf)<sub>3</sub>-Only-Catalyzed Glycosylation via Activation of an Alkyne Appended with an Amide Auxiliary Group
We herein present the development of a novel glycosylation protocol using glycosyl <i>o</i>-<i>N</i>-(<i>o</i>-methoxybenzamidoyl)-propynyl benzoates as donors, activated solely by a catalytic amount of In(OTf)<sub>3</sub>, eliminating the need for a Au(I) catalyst. This approach offers mild and orthogonal conditions, enabling glycosylation across a broad substrate scope and facilitating versatile one-pot strategies for glycan assembly. Mechanistic insights suggest that In(OTf)<sub>3</sub> serves dual roles by being recruited to the auxiliary group through σ-coordination while activating the alkyne via π-interaction.
Authors
- Menghan Li (ORCID: https://orcid.org/0000-0002-5464-3031)
- Houchao Tao (ORCID: https://orcid.org/0000-0001-7598-0275)
- Y. L. Qiu (ORCID: https://orcid.org/0000-0003-0524-1762)
- Liya Yang
- Yan Ren (ORCID: https://orcid.org/0000-0002-4007-8625)
- Xiangwei Zheng (ORCID: https://orcid.org/0000-0001-5616-9284)
- Wei Gu (ORCID: https://orcid.org/0000-0001-5908-1616)
- Xiaodi Yang (ORCID: https://orcid.org/0000-0002-6952-8909)
- Zijie Zhou (ORCID: https://orcid.org/0009-0001-4410-339X)
- Lingyun Pan (ORCID: https://orcid.org/0000-0002-9979-5645)
- Yan Tan (ORCID: https://orcid.org/0000-0003-0938-7996)
- Yulong Zhu
Institutions
- Shanghai University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-10
- DOI
- https://doi.org/10.1021/acs.orglett.5c00219
- Citations
- 3
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Shanghai University of Traditional Chinese Medicine