Cascade Aza-Prins/Friedel–Crafts Reaction of Homocinnamyloxycarbamate and Aromatic Aldehydes Yielding Aromatic Ring-Annulated Hydrocyclopenta-1,2-oxazinane DOI

Tinatina Junior Kindala,

Kazuhiko Takatori, Shinji Nagumo

et al.

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

Cascade Aza-Prins/Friedel–Crafts Reaction of Homocinnamyloxycarbamate and Aromatic Aldehydes Yielding Aromatic Ring-Annulated Hydrocyclopenta-1,2-oxazinane DOI

Tinatina Junior Kindala,

Kazuhiko Takatori, Shinji Nagumo

et al.

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

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