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Issue 68, 2014
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Diels–Alder reactions of pinacol alkenylboronates: an experimental and theoretical study

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Abstract

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.

Graphical abstract: Diels–Alder reactions of pinacol alkenylboronates: an experimental and theoretical study

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Supplementary files

Article information


Submitted
22 Jul 2014
Accepted
01 Aug 2014
First published
01 Aug 2014

RSC Adv., 2014,4, 36385-36400
Article type
Paper
Author version available

Diels–Alder reactions of pinacol alkenylboronates: an experimental and theoretical study

M. M. Vallejos, N. Grimblat and S. C. Pellegrinet, RSC Adv., 2014, 4, 36385
DOI: 10.1039/C4RA07415G

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