Asymmetric Organocatalyzed Michael/Oxa-Michael Domino Reaction of Isoxazole-5-ones with 1,3-Nitroenynes: Access to Chiral Fused Dihydropyranisoxazolines
Abstract
Enantioselective synthesis of fused dihydropyranisoxazoles has been achieved through an organocatalyzed Michael/oxa-Michael domino reaction between branched nitroenynes and 3-arylisoxazol-5(4 H )-ones. This protocol explores the rare reactivity of 3-arylisoxazol-5(4 H )-ones as bisnucleophiles from C-4 and exocyclic carbonyl oxygen atoms in enantioselective reactions. The versatility of the resulting bicyclic dihydropyranoisoxazoline framework has been showcased through a series of intriguing post-synthetic transformations, underscoring its potential in complex molecule construction.
Fields of Study & Subjects
Asymmetric Synthesis and Catalysis
Synthesis of heterocyclic compounds
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 5
- Pages
- 2215–2226
- Publication date
- 25 January 2026
- Language
- EN