Artículo
Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
Fecha de publicación:
08/2014
Editorial:
Royal Society of Chemistry
Revista:
RSC Advances
ISSN:
2046-2069
e-ISSN:
2046-2069
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
Palabras clave:
Diels-Alder
,
Alkenylboronates
,
Dft
,
Reversibility
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Colecciones
Articulos(CCT - NORDESTE)
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - NORDESTE
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - NORDESTE
Citación
Vallejos, Margarita; Grimblat, Nicolas; Pellegrinet, Silvina Carla; Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study; Royal Society of Chemistry; RSC Advances; 4; 68; 8-2014; 36385-36400
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