Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3<i>H</i>)-furanone Scaffolds
In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3<i>H</i>)-furanone skeletons. The cascade cycloaddition proceeds via the 2(5<i>H</i>)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate for phosphine catalysis. These findings highlight the significant potential of harnessing vinyl oxiranes as versatile synthons for constructing spirocyclic compounds through simultaneous multicyclic skeleton formation.
Authors
- Xin Zhao
- Chung‐Ming Sun (ORCID: https://orcid.org/0000-0002-1804-1578)
- Hongchao Guo (ORCID: https://orcid.org/0000-0002-7356-4283)
- Chang Wang (ORCID: https://orcid.org/0000-0003-2870-6518)
- Haiyang Wang (ORCID: https://orcid.org/0000-0001-5200-3965)
- Jiaxin Qu
- Wei Du (ORCID: https://orcid.org/0000-0001-5853-6762)
- Thomas P. Yang (ORCID: https://orcid.org/0009-0000-7002-7020)
- Chia‐Yu Wu
Institutions
- Shandong First Medical University (CN)
- China Agricultural University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-09
- DOI
- https://doi.org/10.1021/acs.orglett.4c03633
- Citations
- 3
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- Natural Science Foundation of Shandong Province
- Shandong First Medical University