南方科技大学知识苑(SUSTech KC): Asymmetric Hydrogenation of Racemic 2-Substituted Indoles via Dynamic Kinetic Resolution: An Easy Access to Chiral Indolines Bearing Vicinal Stereogenic Centers

题名	Asymmetric Hydrogenation of Racemic 2-Substituted Indoles via Dynamic Kinetic Resolution: An Easy Access to Chiral Indolines Bearing Vicinal Stereogenic Centers
作者	Rong, Nianxin 1; Zhou, Ao1,2 ; Liang, Mingrong 1; Wang, Shou-Guo 1; Yin, Qin 1
通讯作者	Yin, Qin
发表日期	2024-02-15
DOI	10.1021/jacs.4c00298
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 影响因子和分区
ISSN	0002-7863
EISSN	1520-5126
卷号	146 期号:8
摘要	The asymmetric hydrogenation (AH) of N-unprotected indoles is a straightforward, yet challenging method to access biologically interesting NH chiral indolines. This method has for years been limited to 2/3-monosubstituted or 2,3-disubstituted indoles, which produce chiral indolines bearing endocyclic chiral centers. Herein, we have reported an innovative Pd-catalyzed AH of racemic alpha-alkyl or aryl-substituted indole-2-acetates using an acid-assisted dynamic kinetic resolution (DKR) process, affording a range of structurally fascinating chiral indolines that contain exocyclic stereocenters with excellent yields, diastereoselectivities, and enantioselectivities. Mechanistic studies support that the DKR process relies on a rapid interconversion of each enantiomer of racemic substrates, leveraged by an acid-promoted isomerization between the aromatic indole and nonaromatic exocyclic enamine intermediate. The reaction can be performed on a gram scale, and the products can be derivatized into non-natural beta-amino acids via facile debenzylation and amino alcohol upon reduction.
相关链接	[来源记录]
收录类别	SCI ; EI
语种	英语
学校署名	其他
资助项目	Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences["22071097","22271307"] ; National Natural Science Foundation of China[2021B1515020062]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:001167228800001
出版者	AMER CHEMICAL SOC
来源库	Web of Science
引用统计	被引频次[WOS]：5
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/789085
专题	南方科技大学
作者单位	1.Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Peoples R China 2.Southern Univ Sci & Technol, Shenzhen 518055, Peoples R China
推荐引用方式 GB/T 7714	Rong, Nianxin,Zhou, Ao,Liang, Mingrong,et al. Asymmetric Hydrogenation of Racemic 2-Substituted Indoles via Dynamic Kinetic Resolution: An Easy Access to Chiral Indolines Bearing Vicinal Stereogenic Centers[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024,146(8).
APA	Rong, Nianxin,Zhou, Ao,Liang, Mingrong,Wang, Shou-Guo,&Yin, Qin.(2024).Asymmetric Hydrogenation of Racemic 2-Substituted Indoles via Dynamic Kinetic Resolution: An Easy Access to Chiral Indolines Bearing Vicinal Stereogenic Centers.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,146(8).
MLA	Rong, Nianxin,et al."Asymmetric Hydrogenation of Racemic 2-Substituted Indoles via Dynamic Kinetic Resolution: An Easy Access to Chiral Indolines Bearing Vicinal Stereogenic Centers".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146.8(2024).