Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination

doi:10.1038/s41467-023-40718-8

	Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination
	Yu, Shaoze; Bao, Hanyang; Zhang, Dekun; Yang, Xiaoyu
	2023-08
发表期刊	NATURE COMMUNICATION (IF:14.7[JCR-2023],16.1[5-Year])
ISSN	2041-1723
EISSN	2041-1723
卷号	14 期号:1
发表状态	已发表
DOI	10.1038/s41467-023-40718-8
摘要	Planar chiral [2.2]paracyclophane derivatives are a type of structurally intriguing and practically useful chiral molecules, which have found a range of important applications in the field of asymmetric catalysis and material science. However, access to enantioenriched [2.2]paracyclophanes represents a longstanding challenge in organic synthesis due to their unique structures, which are still highly dependent on the chiral chromatography separation technique and classical chemical resolution strategy to date. In this work, we report on an efficient and versatile kinetic resolution protocol for various substituted amido[2.2]paracyclophanes, including those with pseudo-geminal, pseudo-ortho, pseudo-meta and pseudo-para disubstitutions, using chiral phosphoric acid (CPA)-catalyzed asymmetric amination reaction, which was also applicable to the enantioselective desymmetrization of an achiral diamido[2.2]paracyclophane. Detailed experimental studies shed light on a new reaction mechanism for the electrophilic aromatic C-H amination, which proceeded through sequential triazane formation and N[1,5]-rearrangement. The facile large-scale kinetic resolution reaction and diverse derivatizations of both the recovered chiral starting materials and the C-H amination products showcased the potential of this method.
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收录类别	SCI
语种	英语
资助项目	The authors gratefully acknowledge NSFC (grant nos. 22171186, 22222107), Double First-Class Initiative Fund of ShanghaiTech University, and ShanghaiTech University start-up funding for financial support. The authors thank the support from Analytical Instru["22222107","SPST-AIC10112914"] ; null[22171186]
WOS研究方向	Science & Technology - Other Topics
WOS类目	Multidisciplinary Sciences
WOS记录号	WOS:001057573200004
出版者	NATURE PORTFOLIO
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/329017
专题	物质科学与技术学院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_硕士生物质科学与技术学院_博士生
通讯作者	Yang, Xiaoyu
作者单位	ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, 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	Yu, Shaoze,Bao, Hanyang,Zhang, Dekun,et al. Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination[J]. NATURE COMMUNICATION,2023,14(1).
APA	Yu, Shaoze,Bao, Hanyang,Zhang, Dekun,&Yang, Xiaoyu.(2023).Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination.NATURE COMMUNICATION,14(1).
MLA	Yu, Shaoze,et al."Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination".NATURE COMMUNICATION 14.1(2023).