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Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2020 Mar 06; Vol. 85 (5), pp. 3560-3567. Date of Electronic Publication: 2020 Feb 20. - Publication Year :
- 2020
-
Abstract
- A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 85
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32013428
- Full Text :
- https://doi.org/10.1021/acs.joc.9b03279