Progress in the Development of Diels-Alder Reactions of Organoboron Compounds

DEZOTTI FEDERICO; NOELIA S. MEDRAN; NATALIA LABADIE,; RAMOS MARCHENA JUAN M.; DEZOTTI FEDERICO; NOELIA S. MEDRAN; NATALIA LABADIE,; RAMOS MARCHENA JUAN M.

Conferencia; Empowering Women in Organic Chemistry; 2020

Empowering Women in Organic Chemistry

The Diels-Alder reaction (DA) is unquestionably one of the most prominent reactions of organicchemistry, offering synthetic access to a wide variety of six-membered ring structures with welldefined stereochemistry. The DA reactions of boron-substituted substrates have great potential dueto their intriguing mechanistic features, the accessibility of diverse unsaturated organoboroncompounds and the possibility of subsequent functional group transformations. Our group hasstudied and described the reactivity of varied boron-substituted alkenes and alkynes as dienophiles.Later on, we began exploring the use of boron-substituted heterocycles as dienes. Herein, wepresent the most recent advances in our research. We were able to expand the range of DAreactions of boron-substituted dienes. The DA reactions of several boron-substituted furans at C-2 and C-3 with N-phenylmaleimide were investigated, resulting in the generation of stable adductswith excellent yields and exo diastereoselectivities. In addition, we report the novel use of a boronsubstituted allene as a DA dienophile. The reactivity of allenylboronic acid pinacol ester withcyclopentadiene was studied experimentally and the mechanisms for the competing pathways wereexplored theoretically. Currently, we are investigating the DA reactions with other reactionpartners as well as the further functionalization of the cycloadducts.