Regioselective Ring-Opening of Oxetanes Catalyzed by Lewis Superacid $\mathrm{Al(C)_{6}F_{5})_{3}}$
This study details an aluminum-catalyzed regioselective isomerization of 2,2-disubstituted oxetanes to yield homoallylic alcohols. The reaction takes place in toluene at 40 °C, employing 1 mol % of $\mathrm{Al(C)_{6}F_{5})_{3}}$ as catalyst. This catalytic system shows a wide substrate scope (12 exa...
| Autores: | , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2024 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:dnet:ubarcelona__::3daf918210f32cf7d9599750788432cf |
| Acceso en línea: | https://hdl.handle.net/2445/229322 |
| Access Level: | acceso abierto |
| Palabra clave: | Alcaloides Aldehids Síntesi inorgànica Alkaloids Aldehydes Inorganic synthesis (Chemistry) |
| Sumario: | This study details an aluminum-catalyzed regioselective isomerization of 2,2-disubstituted oxetanes to yield homoallylic alcohols. The reaction takes place in toluene at 40 °C, employing 1 mol % of $\mathrm{Al(C)_{6}F_{5})_{3}}$ as catalyst. This catalytic system shows a wide substrate scope (12 examples). The optimized conditions are especially useful for electron-rich aryl oxetanes, completely suppressing the formation of allyl isomers and reducing the amount of the dimer by-product. The synthetic applicability of the reported methodology is demonstrated by the enantioselective formal synthesis of curcuquinone and the σ1 receptor agonist RC-33. |
|---|