The reaction of transient ortho-thioquinones, which act as electron-poor dienes, with properly designed bis-dienophiles leads to the formation of helical-shaped bis-benzoxathiine cycloadducts with complete control of the regiochemistry and the relative stereochemistry. Bis-benzoxathiines were the result of two consecutive inverse-electron-demand cycloaddition processes with stereospecific approach of the diene anti to the bis-dienophile. The helical-shaped structure of the final products was demonstrated spectroscopically and confirmed by single-crystal X-ray analysis.
Helical-Shaped Bis-1,4-benzoxathiines through an Inverse-Electron-Demand Hetero-Diels–Alder Reaction of ortho-Thioquinones / Caterina Viglianisi, ; Stefano Menichetti, ; Sara Piantini, ; Tofani, Lorenzo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2016), pp. 5386-5392. [10.1002/ejoc.201600850]
Helical-Shaped Bis-1,4-benzoxathiines through an Inverse-Electron-Demand Hetero-Diels–Alder Reaction of ortho-Thioquinones
VIGLIANISI, CATERINA;MENICHETTI, STEFANO;PIANTINI, SARA;TOFANI, LORENZO
2016
Abstract
The reaction of transient ortho-thioquinones, which act as electron-poor dienes, with properly designed bis-dienophiles leads to the formation of helical-shaped bis-benzoxathiine cycloadducts with complete control of the regiochemistry and the relative stereochemistry. Bis-benzoxathiines were the result of two consecutive inverse-electron-demand cycloaddition processes with stereospecific approach of the diene anti to the bis-dienophile. The helical-shaped structure of the final products was demonstrated spectroscopically and confirmed by single-crystal X-ray analysis.File | Dimensione | Formato | |
---|---|---|---|
2016_EurJOrgChem_5386–5392.pdf
Accesso chiuso
Tipologia:
Pdf editoriale (Version of record)
Licenza:
Tutti i diritti riservati
Dimensione
938.61 kB
Formato
Adobe PDF
|
938.61 kB | Adobe PDF | Richiedi una copia |
I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.