Stereoselective Synthesis of <i>C‐</i>Vinyl Glycosides via Nickel‐Catalyzed Cross‐Electrophile Couplings of 1,2‐Glycosyl Orthoesters and Vinyl Halides
Comprehensive Summary A highly stereoselective nickel‐catalyzed cross‐electrophile coupling of readily accessible, novel, stable oxygen‐based glycosyl radical precursors, specifically 1,2‐glycosyl orthoesters, is developed. This approach offers an effective pathway to synthesize diverse C ‐vinyl glycosides, characterized by good yields, excellent stereoselectivity, mild reaction conditions, a broad substrate scope, and versatile transformations of the resulting products.
Authors
- Shiyin Zhao (ORCID: https://orcid.org/0009-0007-4353-6509)
- Feng Zhu (ORCID: https://orcid.org/0000-0003-3012-789X)
- Bo Yang (ORCID: https://orcid.org/0000-0003-0612-5712)
- Anrong Chen
- Xin Wang (ORCID: https://orcid.org/0000-0002-4154-0404)
- Xing Zhang (ORCID: https://orcid.org/0000-0002-2699-3448)
- Qiang Tao (ORCID: https://orcid.org/0000-0002-6357-5552)
Institutions
- Nanjing Normal University (CN)
- Shanghai Jiao Tong University (CN)
- Shanghai Innovative Research Center of Traditional Chinese Medicine (CN)
- Henan Institute of Technology (CN)
- Xinxiang University (CN)
Publication Details
- Journal
- Chinese Journal of Chemistry
- Published
- 2024-08-21
- DOI
- https://doi.org/10.1002/cjoc.202400651
- Citations
- 12
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- Natural Science Foundation of Shanghai
- National Science Foundation of Sri Lanka
- National Key Research and Development Program of China
- Fundamental Research Funds for the Central Universities