Enantioselective Palladium(II)-Catalyzed Desymmetrizative Coupling of 7-Azabenzonorbornadienes with Alkynylanilines
Junjie Meng
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
These authors contributed equally to this work
] co-first authors
Search for more papers by this authorHui He
Department of Chemistry, Shantou University, Shantou, 515063 Guangdong, China
These authors contributed equally to this work
] co-first authors
Search for more papers by this authorQianru Liu
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
Search for more papers by this authorProf. Hanhong Xu
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Huicai Huang
Key Laboratory of Chinese Medicinal Resource from Lingnan, Ministry of Education, School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou, 510641 Guangdong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Shao-Fei Ni
Department of Chemistry, Shantou University, Shantou, 515063 Guangdong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhaodong Li
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
National Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023 Jiangsu, China
Search for more papers by this authorJunjie Meng
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
These authors contributed equally to this work
] co-first authors
Search for more papers by this authorHui He
Department of Chemistry, Shantou University, Shantou, 515063 Guangdong, China
These authors contributed equally to this work
] co-first authors
Search for more papers by this authorQianru Liu
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
Search for more papers by this authorProf. Hanhong Xu
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Huicai Huang
Key Laboratory of Chinese Medicinal Resource from Lingnan, Ministry of Education, School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou, 510641 Guangdong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Shao-Fei Ni
Department of Chemistry, Shantou University, Shantou, 515063 Guangdong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhaodong Li
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641 Guangdong, China
National Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023 Jiangsu, China
Search for more papers by this authorThese authors contributed equally to this work
] co-first authors
Graphical Abstract
A palladium-catalyzed enantioselective desymmetrizative coupling of prochiral 7-azabenzonorbornadienes with readily available alkynylanilines afforded dihydronaphthalenes via concomitant generation of three covalent bonds. The methods also allows to build two stereocenters and an indole motif in a highly diastereo- and enantioselective as well as atom-economic manner.
Abstract
A PdII-catalyzed, domino enantioselective desymmetrizative coupling of 7-azabenzonorbornadienes with alkynylanilines is disclosed herein. This operationally simple transformation generates three covalent bonds and two contiguous stereocenters with excellent enantio- and diastereo-selectivity. The resulting functionalized indole-dihydronaphthalene-amine conjugates served as an appealing platform to streamline the diversity-oriented synthesis (DOS) of other valuable enantioenriched compounds. DFT calculations revealed that the two stabilizing non-covalent interactions contributed to the observed enantioselectivity.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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