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ShanghaiTech University Knowledge Management System
Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination | |
2022-05-23 | |
发表期刊 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year]) |
ISSN | 1433-7851 |
EISSN | 1521-3773 |
发表状态 | 已发表 |
DOI | 10.1002/anie.202201064 |
摘要 | An efficient approach for asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been disclosed through enantioselective electrophilic aromatic aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. A wide range of chiral macrocycles bearing varied ring sizes (16 to 23-membered) and functional group-containing ansa chains were readily afforded using this method, with excellent yields and high enantioselectivities (23 examples, up to 99.5 : 0.5 er). Experimental studies and DFT calculations were performed to elucidate the mechanism and origin of stereoselectivities of these reactions. Preliminary utilization of the planar-chiral macrocycle as chiral organocatalyst showcased the potential applications of these novel chiral skeletons. |
关键词 | Amination Asymmetric Catalysis Macrocycles Organocatalysis Paracyclophanes |
URL | 查看原文 |
收录类别 | SCI ; SCIE ; EI ; IC ; CCR |
语种 | 英语 |
资助项目 | NSFC[22171186,21901162,22122104,22193010,21933004] ; Analytical Instrumentation Center, SPST, ShanghaiTech University[SPST-AIC10112914] |
WOS研究方向 | Chemistry |
WOS类目 | Chemistry, Multidisciplinary |
WOS记录号 | WOS:000775068200001 |
出版者 | WILEY-V C H VERLAG GMBH |
引用统计 | 正在获取...
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文献类型 | 期刊论文 |
条目标识符 | https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/171476 |
专题 | 物质科学与技术学院_PI研究组_杨晓瑜组 |
共同第一作者 | Shao, Ying-Bo |
通讯作者 | Xue, Xiao-Song; Yang, Xiaoyu |
作者单位 | 1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China 2.Nankai Univ, Coll Chem, Tianjin 300071, Peoples R China 3.Chinese Acad Sci, Univ Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China 4.Univ Chinese Acad Sci, Sch Chem & Mat Sci, Hangzhou Inst Adv Study, 1 Sub Lane Xiangshan, Hangzhou 310024, Peoples R China |
第一作者单位 | 物质科学与技术学院 |
通讯作者单位 | 物质科学与技术学院 |
第一作者的第一单位 | 物质科学与技术学院 |
推荐引用方式 GB/T 7714 | Wang, Donglei,Shao, Ying-Bo,Chen, Yunrong,et al. Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022. |
APA | Wang, Donglei,Shao, Ying-Bo,Chen, Yunrong,Xue, Xiao-Song,&Yang, Xiaoyu.(2022).Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. |
MLA | Wang, Donglei,et al."Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022). |
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