期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 27, 期 36, 页码 9272-9275出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100829
关键词
Amination; asymmetric catalysis; N,N '-dioxides; nickel; oxindoles
资金
- National Natural Science Foundation of China [U19A2014, 21921002]
In this study, a chiral N,N'-dioxide-nickel(II) complex-catalyzed asymmetric amination method was developed for the synthesis of alkyl or aryl 3-amino-indolinones with quaternary stereocenters in high yields with excellent ee values. The proposed method offers a convenient route to optically active intermediates of 3-amino-2-oxindole-based bioactive compounds, and a possible transition-state model was proposed to elucidate the origin of the chirality based on the X-ray crystal structure of the catalyst and the adduct.
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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