Kinetic Resolution of alpha-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines

doi:10.1021/acscatal.1c02331

	Kinetic Resolution of alpha-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines
	Pan, Yongkai 1; Wang, Donglei1,2,3 ; Chen, Yunrong1 ; Zhang, DeKun1 ; Liu, Wei1 ; Yang, Xiaoyu1
	2021-07-16
发表期刊	ACS CATALYSIS (IF:11.3[JCR-2023],12.6[5-Year])
ISSN	2155-5435
EISSN	2155-5435
卷号	11 期号:14 页码:8443-8448
发表状态	已发表
DOI	10.1021/acscatal.1c02331
摘要	A practical method for kinetic resolution of alpha-tertiary propargylic amines has been achieved via asymmetric remote aminations of anilines with azodicarboxylates enabled by chiral phosphoric acid catalysis. A broad range of aryl and alkyl groups at the alpha-position, as well as the substituted alkynyl and N-aryl groups were well tolerated in these reactions, providing high kinetic resolution performances (with an s-factor up to 111). In addition, the alpha-tertiary amines bearing an alpha-CN group (the Strecker reaction product) could be kinetically resolved with excellent stereoselectivity as well under the same reaction conditions. Fruitful transformations of the chiral amination products and the recovered propargylic amines demonstrated the power of this method in asymmetric synthesis of alpha-tertiary amines and their derivatives.
关键词	kinetic resolution propargylic amines alpha-tertiary amines asymmetric remote amination chiral phosphoric acids Amination Aniline Phosphoric acid Asymmetric synthesis Azodicarboxylates Kinetic resolution Practical method Propargylic amines Reaction conditions Strecker reactions Tertiary amine
收录类别	SCI ; SCIE ; EI
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Physical
WOS记录号	WOS:000674927200005
出版者	AMER CHEMICAL SOC
EI入藏号	20212910648152
EI主题词	Kinetics
EI分类号	802.2 Chemical Reactions ; 804.1 Organic Compounds ; 804.2 Inorganic Compounds ; 931 Classical Physics ; Quantum Theory ; Relativity
原始文献类型	Article
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/127855
专题	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
共同第一作者	Wang, Donglei
通讯作者	Yang, Xiaoyu
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China; 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China; 3.Shanghai Inst Organ Chem, Shanghai 200032, 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	Pan, Yongkai,Wang, Donglei,Chen, Yunrong,et al. Kinetic Resolution of alpha-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines[J]. ACS CATALYSIS,2021,11(14):8443-8448.
APA	Pan, Yongkai,Wang, Donglei,Chen, Yunrong,Zhang, DeKun,Liu, Wei,&Yang, Xiaoyu.(2021).Kinetic Resolution of alpha-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines.ACS CATALYSIS,11(14),8443-8448.
MLA	Pan, Yongkai,et al."Kinetic Resolution of alpha-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines".ACS CATALYSIS 11.14(2021):8443-8448.