A facile microwave-assisted Diels-Alder reaction of vinylboronatesElectronic supplementary information (ESI) available: Experimental procedures, spectroscopic and analytic data and NMR spectra for all compounds. See DOI: 10.1039/c0ob00020e

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...

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Bibliographic Details
Main Authors: Sarotti, Ariel M, Pisano, Pablo L, Pellegrinet, Silvina C
Format: Article
Language:English
Online Access:Get full text
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Summary: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. 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00020e