title: Theoretical investigation of the Diels-Alder reactions of unsaturated boronates.
abstract: The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reactions are concerted normal electron-demand Diels-Alder reactions with asynchronous transition structures and weak [4 + 3] C-B secondary orbital interactions, which explains the low experimental reactivity. Both electronic and steric effects contribute to give the observed low stereo- and regioselectivities.
authors: Instituto de Química Rosario (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario (2000), Argentina.
authors: Nicolás
authors: N
authors: Grimblat
authors: Silvina C
authors: SC
authors: Pellegrinet
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003198:Computer Simulation; D061565:Cycloaddition Reaction; D004583:Electrons; D008956:Models, Chemical; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001897:Boronic Acids