Highly Regio- and Diastereoselective 1,3-DC Reaction of BDAs and Nitrones: Synthesis of the Spiro[benzofuran-2,5′-isoxazolidine] Framework
A novel series of spiro[benzofuran-2,5'-isoxazolidine] compounds was successfully synthesized using a catalyst-free 1,3-DC reaction between benzofuran-derived azadienes (BDAs) and nitrones. This methodology achieved high regio- and diastereoselectivity and demonstrated remarkable tolerance toward various functional groups in both BDAs and nitrones, yielding products with good to excellent efficiencies (79-99%). Gram-scale synthesis and subsequent functional transformations further validated the application value of this method for further functionalization.
Authors
- Bo Zhu (ORCID: https://orcid.org/0000-0001-8231-5169)
- Chaoyang Jiang
- Shuhong Wang (ORCID: https://orcid.org/0000-0003-0629-7004)
- Junbiao Chang
- W. Xie
- Chenyang Guo (ORCID: https://orcid.org/0009-0005-3758-8447)
Institutions
- Anyang Institute of Technology (CN)
- Henan Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-13
- DOI
- https://doi.org/10.1021/acs.joc.5c00453
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
- Central Plains Scholars and Scientists Studio Fund