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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...

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Bibliographic Details
Published in:RSC advances 2014-01, Vol.4 (68), p.36385-36400
Main Authors: Vallejos, Margarita M., Grimblat, Nicolás, Pellegrinet, Silvina C.
Format: Article
Language:English
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Summary: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.
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA07415G