Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization
2024
Source PublicationADVANCED SCIENCE
ISSN2198-3844
EISSN2198-3844
Status已发表
DOI10.1002/advs.202403125
Abstract

Axially chiral diaryl ethers represent a distinct class of atropisomers,characterized by a unique dual C─O axes system, which have been found in avariety of natural products, pharmaceuticals, and ligands. However, thecatalytic enantioselective synthesis of these atropoisomers poses significantchallenges, due to the difficulty in controlling both chiral C─O axes, and theirmore flexible conformations. Herein, an efficient protocol for catalyticenantioselective synthesis of axially chiral diaryl ethers is presented usingorganocatalyzed asymmetric Povarov reaction-enabled desymmetrization,followed by aromatizations. This method yields a wide range of novelquinoline-based diaryl ether atropoisomers in good yields and highenantioselectivities. Notably, various aromatization protocols are developed,resulting in a diverse set of polysubstituted quinoline-containing diaryl etheratropisomers. Thermal racemization studies suggested excellentconfigurational stabilities for these novel diaryl ether atropisomers (withracemization barriers up to 38.1 kcal mol−1 ). Moreover, this researchdemonstrates for the first time that diaryl ether atropisomers lacking the bulkyt-Bu group can still maintain a stable configuration, challenging the priorknowledge in the field. The fruitful derivatizations of the functional group-richchiral products further underscore the value of this method.

Indexed BySCI
Language英语
Citation statistics
Document Type期刊论文
Identifierhttps://kms.shanghaitech.edu.cn/handle/2MSLDSTB/421388
Collection物质科学与技术学院_博士生
物质科学与技术学院_PI研究组_杨晓瑜组
物质科学与技术学院_PI研究组_刘巍组
物质科学与技术学院_硕士生
Corresponding AuthorXiaoyu Yang
Affiliation
Shanghaitech University
First Author AffilicationShanghaiTech University
Corresponding Author AffilicationShanghaiTech University
First Signature AffilicationShanghaiTech University
Recommended Citation
GB/T 7714
Zidan Ye,Wansen Xie,Wei Liu,et al. Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization[J]. ADVANCED SCIENCE,2024.
APA Zidan Ye,Wansen Xie,Wei Liu,Changyu Zhou,&Xiaoyu Yang.(2024).Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization.ADVANCED SCIENCE.
MLA Zidan Ye,et al."Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization".ADVANCED SCIENCE (2024).
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