Regioselective Ring-Opening of Oxetanes Catalyzed by Lewis Superacid Al(C6F5)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 Al(C6F5)3 as catalyst. This catalytic system shows a wide substrate scope (12 examples). The optimized...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2024 |
| País: | España |
| Institución: | Universitat Autònoma de Barcelona |
| Repositorio: | Dipòsit Digital de Documents de la UAB |
| Idioma: | inglés |
| OAI Identifier: | oai:ddd.uab.cat:288487 |
| Acceso en línea: | https://ddd.uab.cat/record/288487 https://dx.doi.org/urn:doi:10.1002/adsc.202301183 |
| Access Level: | acceso abierto |
| Palabra clave: | Catalysis Asymmetric hydrogenation Lewis superacid Natural product synthesis Oxetanes Isomerization Tris(pentafluorophenyl)alane |
| 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 Al(C6F5)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. |
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