A facile microwave-assisted Diels-Alder reaction of vinylboronates.
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.
Sarotti
Ariel M
AM
Instituto de Química Rosario (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario (2000), Argentina.
Pisano
Pablo L
PL
Pellegrinet
Silvina C
SC
D001897:Boronic Acids / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D008872:Microwaves; D008956:Models, Chemical; D010084:Oxidation-Reduction; D014753:Vinyl Compounds / Q000737:chemistry*
D001897:Boronic Acids; D014753:Vinyl Compounds