Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate.
J Am Chem Soc
; 135(22): 8169-72, 2013 Jun 05.
Article
em En
| MEDLINE
| ID: mdl-23672506
ABSTRACT
Herein we report a highly enantioselective synthesis of polycyclic indoles and pyrroles with up to 99% ee by an iridium catalyst system consisting of a commercially available iridium precursor and a readily accessible ligand. Investigation of the reaction mechanism led to the discovery of an unprecedented dearomatized spiro intermediate and its in situ migration phenomenon. The new reaction mode features switching of the substituent from the indole C-3 position to the C-2 position (from the C-2 position to the C-3 position in the case of pyrrole) without loss of the enantiomeric purity, providing a novel concept in designing the asymmetric construction of enantiopure polycyclic indoles and pyrroles.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirróis
/
Compostos de Espiro
/
Indóis
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
China