首页|Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles

Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles

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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 essen-tial for high enantioselectivity of the products.This could be due to the additional interaction between the ester group and the cata-lyst,as well as the intramolecular hydrogen bonding.Our findings provide a new strategy for the asymmetric construction of 2-arylindole atropisomers.

Chiral phosphoric acidQuinonediiminesDirect aminationNucleophilic additionAsymmetric catalysisEnantioselectivityAxially chiral 2-arylindoleAtroposelective synthesis

Wen Bao、Ye-Hui Chen、Yu-Wei Liu、Shao-Hua Xiang、Bin Tan

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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

国家重点研发计划国家重点研发计划国家自然科学基金国家自然科学基金国家自然科学基金Guangdong Innovative Program深圳市科技计划深圳市科技计划深圳市科技计划assistance of SUSTech Core Research Facilities

2022YFA15037032021YFF07016042182510522231004222711352019BT02Y335KQTD20210811090112004JCYJ20210324120205016JCYJ20210324105005015

2024

10.1002/cjoc.202300589

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(7)
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