Regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters

doi:10.1039/d1qo00720c

	Regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters
	He, Faqian1,2,3 ; Wang, Jiawen1 ; Zhou, Fang4 ; Tao, Houchao4 ; Yang, Xiaoyu1
	2021-10-07
发表期刊	ORGANIC CHEMISTRY FRONTIERS (IF:4.6[JCR-2023],4.3[5-Year])
ISSN	2052-4129
EISSN	2052-4129
卷号	8 期号:19 页码:5377-5382
发表状态	已发表
DOI	10.1039/d1qo00720c
摘要	The direct regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates alpha-hydrazido-alpha-alkynyl ketone products with high enantioselectivity. Control experiments indicate that the alpha-alkynyl group in the ketone substrate is critical for both the reactivity and stereoselectivity of the reaction. Facile derivatizations of the functional group-abundant chiral product further highlight the value of this approach in the asymmetric synthesis of alpha-tertiary amines and N-containing heterocycles.
关键词	Amines Enantioselectivity Acid catalysis Alkynyl groups Alkynyls Azodicarboxylates Control experiments Derivatizations Enantioselective High enantioselectivity Quaternary stereocenters Regio selective
收录类别	SCI ; SCIE ; EI ; IC
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000682975900001
出版者	ROYAL SOC CHEMISTRY
EI入藏号	20214010985690
EI主题词	Ketones
EI分类号	801.4 Physical Chemistry ; 804.1 Organic Compounds
原始文献类型	Article; Early Access
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/127931
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 iHuman研究所_PI研究组_陶厚朝组生命科学与技术学院_博士生
通讯作者	Tao, Houchao; 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; 4.ShanghaiTech Univ, IHuman Inst, 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	iHuman研究所; 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	He, Faqian,Wang, Jiawen,Zhou, Fang,et al. Regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters[J]. ORGANIC CHEMISTRY FRONTIERS,2021,8(19):5377-5382.
APA	He, Faqian,Wang, Jiawen,Zhou, Fang,Tao, Houchao,&Yang, Xiaoyu.(2021).Regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters.ORGANIC CHEMISTRY FRONTIERS,8(19),5377-5382.
MLA	He, Faqian,et al."Regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters".ORGANIC CHEMISTRY FRONTIERS 8.19(2021):5377-5382.