Chiral Phosphoric Acid-Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines

The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-08, Vol.135 (32), p.11740-11743
Main Authors: Saito, Kodai, Shibata, Yukihiro, Yamanaka, Masahiro, Akiyama, Takahiko
Format: Article
Language:English
Subjects:
Catalysis
Hydrogenation
Imines - chemistry
Indoles - chemistry
Kinetics
Oxidation-Reduction
Phosphoric Acids - chemistry
Stereoisomerism
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Summary:The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja406004q