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Atroposelective synthesis of 2-arylindoles via chiral phosphoric acid-catalyzed direct amination of indoles
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  • Wen Bao,
  • Ye-Hui Chen,
  • Yu-Wei Liu,
  • Shao-Hua Xiang,
  • Bin Tan
Wen Bao
Southern University of Science and Technology
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Ye-Hui Chen
Southern University of Science and Technology
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Yu-Wei Liu
Southern University of Science and Technology
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Shao-Hua Xiang
Southern University of Science and Technology
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Bin Tan
Southern University of Science and Technology

Corresponding Author:cjc-tanbin-office@sioc.ac.cn

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Abstract

Indole-based atropisomers are a very important class of axially chiral compounds. However, the atroposelective synthesis of axially chiral 2-arylindole remains largely unexplored. In this study, we report the successful synthesis of atropisomeric 2-arylindoles using direct amination of indoles with p-quinonediimines in the presence of chiral phosphoric acid as a catalyst. Quinonediimine acts as an aminating reagent through formal polarity inversion of imine. The malonate group on the 2-aryl of 2-indoles was found to be essential for high enantioselectivity of the products. This could be due to the additional interaction between the ester group and the catalyst, as well as the intramolecular hydrogen bonding. Our findings provide a new strategy for the asymmetric construction of 2-arylindole atropisomers.
15 Nov 20231st Revision Received
16 Nov 2023Submission Checks Completed
16 Nov 2023Assigned to Editor
16 Nov 2023Review(s) Completed, Editorial Evaluation Pending
22 Nov 2023Editorial Decision: Accept