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Synthesis of Bridged Cycloisoxazoline Scaffolds via Rhodium-Catalyzed Coupling of Nitrones with Cyclic Carbonate
- Source :
- The Journal of Organic Chemistry; 20230101, Issue: Preprints
- Publication Year :
- 2023
-
Abstract
- Bridged isoxazolidines were synthesized via Rh(III)-catalyzed C–H allylation of α-aryl nitrones with 5-methylene-1,3-dioxan-2-one. The nitrone group serves as a directing group and 1,3-dipole in the C–H activation/[3 + 2] cycloaddition cascade, exhibiting excellent chemo- and stereoselectivity along with good functional group compatibility. The resulting skeletal structure was conveniently modified to produce a range of important chemical frameworks, and the protocol was applied to biologically active molecules.
Details
- Language :
- English
- ISSN :
- 00223263
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- The Journal of Organic Chemistry
- Publication Type :
- Periodical
- Accession number :
- ejs64496873
- Full Text :
- https://doi.org/10.1021/acs.joc.3c01840