INVESTIGADORES
VALLEJOS margarita De Las mercedes
artículos
Título:
Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
Autor/es:
VALLEJOS, MARGARITA M.; GRIMBLAT, NICOLÁS; PELLEGRINET, SILVINA C.
Revista:
RSC Advances
Editorial:
Royal Society of Chemistry
Referencias:
Año: 2014 vol. 4 p. 36385 - 36400
ISSN:
2046-2069
Resumen:
We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different 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 shed some light into 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.
