Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: application to the synthesis of the Californian red scale beetle pheromone.
Angew Chem Int Ed Engl
; 51(50): 12444-8, 2012 Dec 07.
Article
en En
| MEDLINE
| ID: mdl-23129403
ABSTRACT
E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAFâ
3 H(2)O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF(2)/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Atractivos Sexuales
/
Boro
/
Alquenos
Límite:
Animals
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2012
Tipo del documento:
Article
País de afiliación:
Reino Unido