The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1514 - 1530

Опубликована: Янв. 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.

Язык: Английский