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A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation |
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| Authors: | Linlong Dai Yuheng Liu Qing Xu Meifang Wang Dr Qiaohong Zhu Prof?Dr Peiyuan Yu Prof?Dr Guofu Zhong Prof?Dr Xiaofei Zeng |
| Institution: | 1. 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;2. College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China;3. Department of Chemistry, Southern University of Science and Technology, Shenzhen, China;4. Department of Chemistry, Eastern Institute for Advanced Study, Ningbo, China |
| Abstract: | 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. |
| Keywords: | Asymmetric Catalysis Axial Chirality Dynamic Kinetic Resolution Ethers Phosphoric Acids |