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

IUPAC

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