A facile microwave-assisted Diels-Alder reaction of vinylboronates

被引：29
|
作者：
Sarotti, Ariel M. [1 ]
Pisano, Pablo L. [1 ]
Pellegrinet, Silvina C. [1 ]
机构：
[1] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, CONICET, RA-2000 Rosario, Santa Fe, Argentina
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 22期
关键词：
AROMATIC BORONIC ESTERS; MODERN ORGANIC-SYNTHESIS; HYDROXY ACRYLIC-ACID; CYCLOADDITION ROUTE; BUILDING-BLOCK; DERIVATIVES; EQUIVALENTS; 4,4,6-TRIMETHYL-2-VINYL-1,3,2-DIOXABORINANE; REAGENT;
D O I：
10.1039/c0ob00020e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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页码：5069 / 5073
页数：5
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