Microwave-assisted Diels-Alder reactions of vinylboronates

SAROTTI, A.M.; PISANO, P.L.; PELLEGRINET, S.C.

Glasgow, Escocia

Simposio; 15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 15); 2009

Due to their great versatility, boron-substituted dienophiles have emerged as attractive building blocks in organic synthesis.1 Alkenylboronates exhibit low reactivity in Diels-Alder reactions.2 However, unlike dialkylboranes, boronates are stable to air and moisture and can be purified by chromatography or distillation. We have recently found that the Diels-Alder reactions of vinylboronates can be easily performed using microwave irradiation3 with excellent yields (>90%) and short reaction times (1-6 h). We will describe the results of the reactions of vinylboronates derived from n-butanol, pinacol and 2-methyl-2,4-pentanediol with a series of structurally diverse dienes.