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

MEDRAN, NOELIA; PELLEGRINET, SILVINA; LABADIE, NATALIA; RAMOS, JUAN; DEZOTTI, FEDERICO

Virtual

Conferencia; Empowering Women in Organic Chemistry (EWOC) 2020; 2020

Empowering Women in Organic Chemistry (EWOC)

The Diels-Alder reaction (DA) is unquestionably one of the most prominent reactions of organic chemistry, offering synthetic access to a ide variety of six-membered ring structures with welldefined stereochemistry. The DA reactions of boron-substituted substrates have great potential due to their intriguing mechanistic features, the accessibility of diverse unsaturated organoboron compounds and the possibility of subsequent functional group transformations. Our group has studied 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, we present the most recent advances in our research. We were able to expand the range of DA reactions of boron-substituted dienes. The DA reactions of several boron-substituted furans at C2 and C-3 with N-phenylmaleimide were investigated, resulting in the generation of stable adducts with 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 with cyclopentadiene was studied experimentally and the mechanisms for the competing pathways were explored theoretically. Currently, we are investigating the DA reactions with other reaction partners as well as the further functionalization of the cycloadducts.