Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2014 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/29060 |
| Acceso en línea: | http://hdl.handle.net/11336/29060 |
| Access Level: | acceso abierto |
| Palabra clave: | Diels-Alder Alkenylboronates Dft Reversibility https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide. |
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