IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Theoretical investigation of the Diels?Alder reactions of unsaturated boronates
Autor/es:
PELLEGRINET, S. C.; GRIMBLAT, N.
Revista:
ORGANIC & BIOMOLECULAR CHEMISTRY
Editorial:
ROYAL SOC CHEMISTRY
Referencias:
Lugar: CAMBRIDGE; Año: 2013 vol. 11 p. 3733 - 3741
ISSN:
1477-0520
Resumen:
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 e ff ect 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 e ff ects contribute to give the observed low stereo- and regioselectivities.
