中文版 | English
Title

A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation

Author
Corresponding AuthorZhong, Guofu; Zeng, Xiaofei
Publication Years
2023-02-06
DOI
Source Title
ISSN
1433-7851
EISSN
1521-3773
Volume62
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.
© 2022 Wiley-VCH GmbH.
Indexed By
EI ; SCI
Language
English
Important Publications
NI Journal Papers
SUSTech Authorship
Others
Funding Project
We gratefully acknowledge the Natural Science Foundation of China (No. 22171064), the Natural Science Foundation of Zhejiang Province (LY18B020015), the Hangzhou Science and Technology Development Project (20191203B15) and Hangzhou Normal University for financial support.
WOS Accession No
WOS:000910085200001
Publisher
EI Accession Number
20230213373549
EI Keywords
Aniline ; Bioactivity ; Catalysis ; Catalysts ; Chelation ; Enantioselectivity ; Hydrogenation ; Kinetics ; Ligands ; Stereochemistry
ESI Classification Code
Medicine and Pharmacology:461.6 ; Fluid Flow, General:631.1 ; Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804 ; Organic Compounds:804.1 ; Classical Physics; Quantum Theory; Relativity:931
ESI Research Field
CHEMISTRY
Data Source
EV Compendex
Citation statistics
Cited Times [WOS]:1
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/519678
DepartmentDepartment of Chemistry
Affiliation
1.College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China
2.Department of Chemistry, Eastern Institute for Advanced Study, Ningbo, China
3.School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, China
4.Department of Chemistry, Southern University of Science and Technology, Shenzhen, China
Recommended Citation
GB/T 7714
Dai, Linlong,Liu, Yuheng,Xu, Qing,et al. A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62.
APA
Dai, Linlong.,Liu, Yuheng.,Xu, Qing.,Wang, Meifang.,Zhu, Qiaohong.,...&Zeng, Xiaofei.(2023).A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62.
MLA
Dai, Linlong,et al."A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62(2023).
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