Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combinat...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-01, Vol.56 (4), p.623-626
Main Authors: Lu, Fo-Yun, Chen, Yu-Jue, Chen, Yuan, Ding, Xuan, Guan, Zhi, He, Yan-Hong
Format: Article
Language:English
Subjects:
Alkylation
Anodizing
Crystallography
Electrochemistry
Enantiomers
Oxidation
Proline
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Summary:A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions. An asymmetric electrosynthesis is developed by combining anodic oxidation and proline-catalysis to realize enantioselective synthesis of C2-quaternary indolin-3-ones from 2-arylindoles.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09178e