Synthesis of novel isoxazoline and isoxazolidine derivatives: carboxylic acids and delta bicyclic lactones via the nucleophilic addition of bis(trimethylsilyl)ketene acetals to isoxazoles
Bis(trimethylsilyl)ketene acetals readily react with activated N-triflyl isoxazoles to selectively afford novel isoxazoline or isoxazolidine derivatives. The regioselectivity of the reaction strongly depends on the substrate substituents. When the isoxazole is substituted at the 5-position by a meth...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2021 |
| País: | México |
| Institución: | Universidad Nacional Autónoma de México |
| Repositorio: | Repositorio del Instituto de Química, UNAM |
| Idioma: | inglés |
| OAI Identifier: | oai:rdu.iquimica.unam.mx:20.500.12214/1301 |
| Acceso en línea: | http://rdu.iquimica.unam.mx/handle/20.500.12214/1301 |
| Access Level: | acceso abierto |
| Palabra clave: | info:eu-repo/classification/cti/2 Ketene acetals Isoxazoline Isoxazolidine Lactone N-triflyl activation |
| Sumario: | Bis(trimethylsilyl)ketene acetals readily react with activated N-triflyl isoxazoles to selectively afford novel isoxazoline or isoxazolidine derivatives. The regioselectivity of the reaction strongly depends on the substrate substituents. When the isoxazole is substituted at the 5-position by a methyl or phenyl group, the lactonization product, i.e., the isoxazolidine derivative, is formed as a result of double nucleophilic addition of the ketene acetal. When the isoxazole is not substituted, the main product is the corresponding carboxylic acid, i.e., the isoxazoline derivative. |
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