Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes: Formation of Air-Stable Trialkylboranes.
J Am Chem Soc
; 139(25): 8404-8407, 2017 06 28.
Article
en En
| MEDLINE
| ID: mdl-28565903
ABSTRACT
Seven-membered-ring trans-alkenes undergo rapid, uncatalyzed carboboration reactions to form trialkylboranes as single diastereomers. In contrast with other trialkylboranes, which can ignite in the presence of oxygen, these trialkylboranes are stable in air. Hindered trialkylboranes can undergo reverse hydroboration reactions to form allylic silanes or can be oxidized to afford highly substituted triols. This reaction sequence permits the construction of compounds with up to five consecutive stereocenters. Control experiments and computational studies support a concerted mechanism for the migratory insertion of the alkene into the carbon-boron bond, similar to the mechanism for hydroboration.
Texto completo:
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Boranos
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Alquenos
Idioma:
En
Revista:
J Am Chem Soc
Año:
2017
Tipo del documento:
Article
País de afiliación:
Estados Unidos