One‐Pot Asymmetric Oxidative Dearomatization of 2‐Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2‐Tetrasubstituted Indolin‐3‐Ones

A one‐pot approach for the asymmetric synthesis of C2‐tetrasubstituted indolin‐3‐ones from 2‐substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2‐substituted indoles...

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Published in:Advanced synthesis & catalysis 2022-03, Vol.364 (7), p.1277-1285
Main Authors: Zhao, Yong‐Long, An, Jian‐Xiong, Yang, Fen‐Fen, Guan, Xiang, Fu, Xiao‐Zhong, Li, Zong‐Qin, Wang, Da‐Peng, Zhou, Meng, Yang, Yuan‐Yong, He, Bin
Format: Article
Language:English
Subjects:
Aldehydes
Asymmetry
C2-tetrasubstituted indolin-3-ones
Catalysis
Drug resistance
Indoles
Ketones
organocatalysis
oxidative dearomatization
Oxidizing agents
Proline
Substitutes
transition metal catalysis
Transition metals
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Summary:A one‐pot approach for the asymmetric synthesis of C2‐tetrasubstituted indolin‐3‐ones from 2‐substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2‐substituted indoles using O2 as green oxidant, and followed by an proline‐promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2‐tetrasubstituted indolin‐3‐ones were obtained in 35–86% yields, 2:1‐>20:1 dr and 48–99% ee. Moreover, the synthetic 2‐tetrasubstituted indolin‐3‐ones could be easily transformed into 1H‐[1,3] oxazino [3,4‐a]indol‐5(3H)‐ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi‐drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101498