DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons
The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives with moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction of vinyl epoxides, simultaneously providing a rare oxygen-containing active intermediate in this field. The gram-scale preparation and facile derivatization of the cycloadduct highlight the significant synthetic potential of this strategy.
Authors
- Chunhao Yuan (ORCID: https://orcid.org/0000-0003-2155-1779)
- 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)
- Jiaxin Qu
- Thomas P. Yang (ORCID: https://orcid.org/0009-0000-7002-7020)
Institutions
- Academy of Medical Sciences (GB)
- Materia (United States) (US)
- Shandong First Medical University (CN)
- China Agricultural University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-24
- DOI
- https://doi.org/10.1021/acs.orglett.4c03502
- Citations
- 4
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Shandong First Medical University