Rapid assembly of functionalised spirocyclic indolines by palladium-catalysed dearomatising diallylation of indoles with allyl acetate.
Chemistry
; 20(41): 13375-81, 2014 Oct 06.
Article
en En
| MEDLINE
| ID: mdl-25171550
ABSTRACT
Herein, we report the application of allyl acetate to the palladium-catalysed dearomatising diallylation of indoles. The reaction can be carried out by using a readily available palladium catalyst at room temperature, and can be applied to a wide range of substituted indoles to provide access to the corresponding 3,3-diallylindolinines. These compounds are versatile synthetic intermediates that readily undergo Ugi reactions or proline-catalysed asymmetric Mannich reactions. Alternatively, acylation of the 3,3-diallylindolinines with an acid chloride or a chloroformate, followed by treatment with aluminium chloride, enables 2,3-diallylindoles to be prepared. By using ring-closing metathesis, functionalised spirocyclic indoline scaffolds can be accessed from the Ugi products, and a dihydrocarbazole can be prepared from the corresponding 2,3-diallylindole.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Paladio
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Compuestos de Espiro
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Compuestos Alílicos
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Indoles
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Acetatos
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2014
Tipo del documento:
Article