A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation
Linlong Dai
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Department of Chemistry, Eastern Institute for Advanced Study, Ningbo, China
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, China
Search for more papers by this authorYuheng Liu
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorQing Xu
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorMeifang Wang
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorDr. Qiaohong Zhu
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorProf. Dr. Peiyuan Yu
Department of Chemistry, Southern University of Science and Technology, Shenzhen, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Guofu Zhong
Department of Chemistry, Eastern Institute for Advanced Study, Ningbo, China
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiaofei Zeng
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorLinlong Dai
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Department of Chemistry, Eastern Institute for Advanced Study, Ningbo, China
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, China
Search for more papers by this authorYuheng Liu
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorQing Xu
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorMeifang Wang
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorDr. Qiaohong Zhu
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorProf. Dr. Peiyuan Yu
Department of Chemistry, Southern University of Science and Technology, Shenzhen, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Guofu Zhong
Department of Chemistry, Eastern Institute for Advanced Study, Ningbo, China
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiaofei Zeng
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
Search for more papers by this authorAbstract
Diaryl ethers are widespread in biologically active compounds, ligands and catalysts. It is known that the diaryl ether skeleton may exhibit atropisomerism when both aryl rings are unsymmetrically substituted with bulky groups. Despite recent advances, only very few catalytic asymmetric methods have been developed to construct such axially chiral compounds. We describe herein a dynamic kinetic resolution approach to axially chiral diaryl ethers via a Brønsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction of dicarbaldehydes with anilines. The desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79 %) and high enantioselectivities (up to 95 % ee) under standard reaction conditions. Such structural motifs are interesting precursors for further transformations and may have potential applications in the synthesis of chiral ligands or catalysts.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the Supporting Information of this article.
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