Sc(OTf)<sub>3</sub>-Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds
In this study, the readily available and inexpensive Sc(OTf)<sub>3</sub> was utilized to activate ortho-benzoyl diazo compounds to in situ generate highly reactive cyclic 1,3-dipoles, which underwent a regioselective [4 + 3] cycloaddition with dioxopyrrolidines, yielding the [4.2.1]-oxabridged scaffolds bearing multiple contiguous quaternary carbon centers with high diastereoselectivities. The method not only exhibited significant economic and operational advantages but also demonstrated practical value through gram-scale synthesis and derivatization experiments.
Authors
- Chenxing Zhou
- Yong Yuan (ORCID: https://orcid.org/0000-0003-3196-1747)
- Congde Huo (ORCID: https://orcid.org/0000-0002-3374-7931)
- Xiazhen Bao (ORCID: https://orcid.org/0000-0003-4658-4227)
- Xudong Wang (ORCID: https://orcid.org/0000-0002-1353-1420)
- Dongsheng Ji
Institutions
- Northwest Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-19
- DOI
- https://doi.org/10.1021/acs.joc.4c02657
- Citations
- 4
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation