The Paternò-Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6-oxabicyclo[3.2.0]heptan-1-ol. The bicyclic structure underwent selective reductive ring opening and acid-catalyzed pinacol-type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism-dependent diastereoselectivity
Stereoselective and regioselective pinacol-type rearrangement of a fused bicyclic oxetanol scaffold
Nicola MelisPrimo
Membro del Collaboration Group
;Alberto LuridianaSecondo
Membro del Collaboration Group
;Francesco SecciMembro del Collaboration Group
;Angelo FrongiaMembro del Collaboration Group
;
2017-01-01
Abstract
The Paternò-Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6-oxabicyclo[3.2.0]heptan-1-ol. The bicyclic structure underwent selective reductive ring opening and acid-catalyzed pinacol-type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism-dependent diastereoselectivity
File in questo prodotto:
| File | Dimensione | Formato | |
|---|---|---|---|
|
Melis_et_al-2017-European_Journal_of_Organic_Chemistry.pdf
Solo gestori archivio
Tipologia:
versione editoriale (VoR)
Dimensione
1.02 MB
Formato
Adobe PDF
|
1.02 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
