Recent Advances in the Development of Diels-Alder Reactions of Unsaturated Organoboron Compounds

RAMOS MARCHENA JUAN M.; PELLEGRINET SILVINA, C.; MEDRAN NOELIA S.; DEZOTTI FEDERICO; TERRESTRE GUSTAVO O.; SIMONETTI SEBASTIÁN O

Boston, Massachusetts, USA

Congreso; 16th Boron Chemistry Meeting in the Americas; 2018

Comité organizador BORAM 2018

The Diels-Alder (DA) reactions of unsaturated boron compounds are fascinatingtransformations with great synthetic potential and interesting mechanistic features. In 2010, we reported that the DA reactions of vinylboronates occurred readily under microwave irradiation. Later, we described the DA reactions of a variety of pinacol alkenylboronic esters. More recently, we proved that α-hydroxyacids accelerate the DA reaction of dibutyl vinylboronate with cyclopentadiene. Theoretical calculations and NMR studies indicated that ligand exchange gives rise to the reactive acyloxyborane species. In the past years we have been devoted to rationally design improved organocatalysts in terms of catalytic activity and enantioselectivity by introducing diverse substituents in the α-hydroxyacid and to extend the scope of the reaction. Also, we have ventured into the development of new DA reactions of other unsaturatedorganoboron compounds. Along these lines, we have found that boron-containing heterocyclic compounds participate in DA reactions. The effect of the substitution pattern has been investigated with experimental and theoretical tools.