Atom Transfer Radical Coupling Enables Highly Enantioselective Carbo-Oxygenation of Alkenes with Hydrocarbons

doi:10.1021/jacs.3c07008

	Atom Transfer Radical Coupling Enables Highly Enantioselective Carbo-Oxygenation of Alkenes with Hydrocarbons
	Jin, Youxiang 4,5; Fan, Lian-Feng 4,5; Ng, Elvis Wang Hei 3,4,5; Yu, Lu 2; Hirao, Hajime 3; Gong, Liu-Zhu 1,4,5
刊名	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
	2023-09-29
卷号	145
ISSN号	0002-7863
DOI	10.1021/jacs.3c07008
通讯作者	Hirao, Hajime(hirao@cuhk.edu.cn) ; Gong, Liu-Zhu(gonglz@ustc.edu.cn)
英文摘要	The selective functionalization of C(sp(3))-H bonds has emerged as a transformative approach for streamlining synthetic routes, offering remarkable efficiency in the preparation and modification of complex organic molecules. However, the direct enantioselective transformation of hydrocarbons to medicinally valuable chiral molecules remains a significant challenge that has yet to be addressed. In this study, we adopt an atom transfer radical coupling (ATRC) strategy to achieve the asymmetric functionalization of C(sp(3))-H bonds in hydrocarbons. This approach involves intermolecular H atom transfer (HAT) between a hydrocarbon and an alkoxy radical, leading to the formation of a carbon-centered radical. The resulting radical adds to alkenes, generating a new radical species that is intercepted by a chiral copper-mediated C-O bond coupling. By employing this method, we can directly access valuable chiral lactones bearing a quaternary stereocenter with high efficiency and excellent enantioselectivity. Importantly, ATRC exhibits great potential as a versatile platform for achieving stereoselective transformations of hydrocarbons.
资助项目	National Key R&D Program of China[2021YFA1500100] ; NSFC[22188101] ; NSFC[21927814] ; Chinese Postdoctoral Science Foundation[2022M713031] ; Anhui Provincial Natural Science Foundation[2208085QB37] ; Youth Innovation Promotion Association CAS[2022455] ; Changjiang Scholarship ; Chinese University of Hong Kong, Shenzhen[UDF01001996] ; Warshel Institute for Computational Biology[C10120180043]
WOS关键词	C-H BONDS ; STEREOSELECTIVE FUNCTIONALIZATION ; ACTIVATION ; BUTOXYL
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:001076145700001
资助机构	National Key R&D Program of China ; NSFC ; Chinese Postdoctoral Science Foundation ; Anhui Provincial Natural Science Foundation ; Youth Innovation Promotion Association CAS ; Changjiang Scholarship ; Chinese University of Hong Kong, Shenzhen ; Warshel Institute for Computational Biology
内容类型	期刊论文
源URL	[http://ir.hfcas.ac.cn:8080/handle/334002/133363]
专题	中国科学院合肥物质科学研究院
通讯作者	Hirao, Hajime; Gong, Liu-Zhu
作者单位	1.Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Peoples R China 2.Chinese Acad Sci, High Magnet Field Lab, Hefei 230031, Peoples R China 3.Chinese Univ Hong Kong, Warshel Inst Computat Biol, Sch Med, Shenzhen 518172, Guangdong, Peoples R China 4.Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China 5.Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
推荐引用方式 GB/T 7714	Jin, Youxiang,Fan, Lian-Feng,Ng, Elvis Wang Hei,et al. Atom Transfer Radical Coupling Enables Highly Enantioselective Carbo-Oxygenation of Alkenes with Hydrocarbons[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2023,145.
APA	Jin, Youxiang,Fan, Lian-Feng,Ng, Elvis Wang Hei,Yu, Lu,Hirao, Hajime,&Gong, Liu-Zhu.(2023).Atom Transfer Radical Coupling Enables Highly Enantioselective Carbo-Oxygenation of Alkenes with Hydrocarbons.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,145.
MLA	Jin, Youxiang,et al."Atom Transfer Radical Coupling Enables Highly Enantioselective Carbo-Oxygenation of Alkenes with Hydrocarbons".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 145(2023).