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Issue 22, 2010
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A facile microwave-assisted Diels–Alder reaction of vinylboronates

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Abstract

The Diels–Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels–Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels–Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.

Graphical abstract: A facile microwave-assisted Diels–Alder reaction of vinylboronates

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Article information


Submitted
19 Apr 2010
Accepted
04 Aug 2010
First published
07 Sep 2010

Org. Biomol. Chem., 2010,8, 5069-5073
Article type
Paper

A facile microwave-assisted Diels–Alder reaction of vinylboronates

A. M. Sarotti, P. L. Pisano and S. C. Pellegrinet, Org. Biomol. Chem., 2010, 8, 5069
DOI: 10.1039/C0OB00020E

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