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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])
ISSN1433-7851
EISSN1521-3773
发表状态已发表
DOI10.1002/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
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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
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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
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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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