Enantioselective Synthesis of 3-Substituted 3-Amino-2-oxindoles by Amination with Anilines.
Chemistry
; 27(36): 9272-9275, 2021 Jun 25.
Article
em En
| MEDLINE
| ID: mdl-33749905
ABSTRACT
A chiral N,N'-dioxide-nickel(II) complex-catalyzed asymmetric amination of 3-bromo-3-substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3-amino-indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3-amino-2-oxindole-based bioactive compounds. Moreover, a possible transition-state model is proposed so as to elucidate the origin of the chirality based on the X-ray crystal structure of the catalyst and the adduct.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Indóis
/
Compostos de Anilina
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article