Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.
J Org Chem
; 77(24): 11034-55, 2012 Dec 21.
Article
en En
| MEDLINE
| ID: mdl-23167569
ABSTRACT
In this Article, a strategy to obtain highly enantioselective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Paladio
/
Compuestos de Espiro
/
Cobre
/
Indoles
/
Lactonas
Idioma:
En
Año:
2012
Tipo del documento:
Article