| 题名 | Synthesis of Axially Chiral QUINAP Derivatives by Ketone-Catalyzed Enantioselective Oxidation |
| 作者 | |
| 通讯作者 | Xiang, Shao-Hua; Tan, Bin |
| 发表日期 | 2023-08-25
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| DOI | |
| 发表期刊 | |
| ISSN | 1433-7851
|
| EISSN | 1521-3773
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| 卷号 | 62期号:40 |
| 摘要 | QUINAPs have emerged as a pivotal class of axially chiral compounds with remarkable features in the stereoinduction of diverse enantioselective transformations. However, the confined substrate range and extravagant price still pose challenges, limiting their broader utilization. Herein, we describe the first atroposelective oxidation of an N atom using a chiral ketone catalyst, allowing the kinetic resolution of QUINAPOs to give both the unreacted substrates and their corresponding N-oxides with excellent enantioselectivity. Importantly, the enantioenriched products can be readily converted into the QUINAP targets without any loss of stereochemical integrity. Mechanistic investigations indicate that a dioxirane, generated through the oxidation of the ketone with oxone, acts as the active catalytic species. Furthermore, we have successfully extended this catalytic system to the kinetic resolution of QUINOLs and the dynamic kinetic transformation of pyridine analogues of QUINAPO possessing a labile stereogenic axis. The practicality of the developed protocol is further demonstrated by the successful application of QUINAPO N-oxide as a Lewis base catalyst in a series of enantioselective transformations. |
| 关键词 | |
| 相关链接 | [来源记录] |
| 收录类别 | |
| 语种 | 英语
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| 重要成果 | NI论文
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| 学校署名 | 通讯
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| 资助项目 | We are grateful for financial support from the National Key Ramp;amp;D Program of China (2022YFA1503703, 2021YFF0701604), the National Natural Science Foundation of China (22231004, 21825105, 22271135), Guangdong Innovative Program (2019BT02Y335), and She["2022YFA1503703","2021YFF0701604"]
; National Key Ramp;amp;D Program of China["22231004","21825105","22271135"]
; National Natural Science Foundation of China[2019BT02Y335]
; Guangdong Innovative Program["KQTD20210811090112004","JCYJ20210324120205016","JCYJ20210324105005015"]
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| WOS研究方向 | Chemistry
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| WOS类目 | Chemistry, Multidisciplinary
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| WOS记录号 | WOS:001060729600001
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| 出版者 | |
| EI入藏号 | 20233514626847
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| EI主题词 | Catalysts
; Catalytic oxidation
; Enantioselectivity
; Ketones
; Kinetics
; Substrates
|
| EI分类号 | Air Pollution Control:451.2
; Fluid Flow, General:631.1
; 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学科分类 | CHEMISTRY
|
| 来源库 | Web of Science
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| 引用统计 |
被引频次[WOS]：11
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| 成果类型 | 期刊论文 |
| 条目标识符 | http://sustech.caswiz.com/handle/2SGJ60CL/559335 |
| 专题 | 理学院_化学系 深圳格拉布斯研究院 |
| 作者单位 | 1.Harbin Inst Technol, Harbin 150001, Peoples R China 2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518055, Peoples R China |
| 第一作者单位 | 化学系; 深圳格拉布斯研究院 |
| 通讯作者单位 | 化学系; 深圳格拉布斯研究院 |
| 推荐引用方式 GB/T 7714 |
Jiang, Peng-Ying,Wu, San,Wang, Guan-Jun,et al. Synthesis of Axially Chiral QUINAP Derivatives by Ketone-Catalyzed Enantioselective Oxidation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(40).
|
| APA |
Jiang, Peng-Ying,Wu, San,Wang, Guan-Jun,Xiang, Shao-Hua,&Tan, Bin.(2023).Synthesis of Axially Chiral QUINAP Derivatives by Ketone-Catalyzed Enantioselective Oxidation.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(40).
|
| MLA |
Jiang, Peng-Ying,et al."Synthesis of Axially Chiral QUINAP Derivatives by Ketone-Catalyzed Enantioselective Oxidation".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.40(2023).
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| 条目包含的文件 | 条目无相关文件。 | |||||
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