The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1514 - 1530
Published: Jan. 17, 2025
The cascade aza-Prins/Friedel-Crafts reaction of homocinnamyloxycarbamate with electron-rich aromatic aldehydes has been successfully established. Most the react carbamate stereoselectively to generate cis-hydroindeno-1,2-oxazinanes. However, reactions benzaldehydes bearing two methoxy groups at meta-positions exhibit a unique stereochemical profile. Furthermore, benzaldehyde three meta- and para-positions proceeds along skeletal rearrangement. Additionally, aza-Prins/Ritter cinnamyloxycarbamate various was found during development reaction. In contrast reaction, gave trans-disubstituted isoxazolidines. These profiles for both were considered on basis several transition-state models.
Language: Английский