Asymmetric Synthesis of ß-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions.
Org Lett
; 21(10): 3563-3567, 2019 05 17.
Article
em En
| MEDLINE
| ID: mdl-31021651
ABSTRACT
The asymmetric Friedel-Crafts alkylation reactions of indoles with ß-substituted cyclopentenimines enabled by chiral phosphoric acid catalysis has been developed, which affords adducts possessing an all-carbon stereocenter with high levels of enantioselectivities. Furthermore, the addition products could be readily converted into two types of useful but previously challenging chiral building blocks, such as ß-alkyl-ß-indolyl cyclopentanones and ß-alkyl-ß-indolyl cyclopentylamides, in one pot via in situ hydrolysis or reduction without erosion of chiral information.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article