Theoretical investigation of the Diels-Alder reactions of unsaturated boronates.
Org Biomol Chem
; 11(22): 3733-41, 2013 Jun 14.
Article
en En
| MEDLINE
| ID: mdl-23629057
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.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Ácidos Borónicos
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Alquenos
/
Reacción de Cicloadición
Idioma:
En
Revista:
Org Biomol Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2013
Tipo del documento:
Article
País de afiliación:
Argentina