Stereoselective Synthesis of Acyclic Tetrasubstituted Alkenes from Anilines by Dearomatization and Trimethylenemethane Cycloaddition
A method for stereoselective construction of acyclic all-carbon tetrasubstituted alkenes through insertion of nitrile-substituted trimethylenemethane into the aryl C–N bond in anilines via an aromaticity destruction-reconstruction process is reported. The process involves dearomatization, azo-[3 + 2...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2022-01, Vol.24 (1), p.314-318 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| Zusammenfassung: | A method for stereoselective construction of acyclic all-carbon tetrasubstituted alkenes through insertion of nitrile-substituted trimethylenemethane into the aryl C–N bond in anilines via an aromaticity destruction-reconstruction process is reported. The process involves dearomatization, azo-[3 + 2] TMM cycloaddition and aromatization-triggered rearrangement. |
|---|---|
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.1c03974 |