Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles†
Wen Bao
School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorYe-Hui Chen
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorYu-Wei Liu
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorShao-Hua Xiang
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorCorresponding Author
Bin Tan
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
E-mail: [email protected]Search for more papers by this authorWen Bao
School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorYe-Hui Chen
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorYu-Wei Liu
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorShao-Hua Xiang
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorCorresponding Author
Bin Tan
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
E-mail: [email protected]Search for more papers by this authorDedicated to the Memory of Professor Xiyan Lu.
Comprehensive Summary
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.
Supporting Information
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