Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by Rh<SUP>II</SUP>/Ru<SUP>II</SUP> Relay Catalysis

doi:10.1021/acs.joc.5c00324

	Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by Rh^II/Ru^II Relay Catalysis
	Li, Xuejiao; Liu, Fang-Jie; Ye, Baihua
	2025-04-25
发表期刊	JOURNAL OF ORGANIC CHEMISTRY (IF:3.3[JCR-2023],3.2[5-Year])
ISSN	0022-3263
EISSN	1520-6904
发表状态	已发表
DOI	10.1021/acs.joc.5c00324
摘要	CpRu-catalyzed asymmetric allylic alkylation serves as a versatile synthetic tool but remains underexplored. Herein, we report a relay system combining achiral Rh2(OAc)4 and a chiral pyridine-oxazoline-ligated Cp*Ru catalyst for asymmetric coupling of cinnamyl chlorides with diazo esters, generating silyl enol ethers in situ as key nucleophilic intermediates. This strategy affords chiral tetrahydrofuran derivatives with two vicinal stereocenters. Catalyst compatibility, excellent regioselectivity, and good enantioselectivity highlight its potential. Computational studies reveal the crucial role of Ru-centered chirality in reaction control.
关键词	Alkylation Allylation Enantioselectivity Reaction intermediates Regioselectivity Stereocenters Stereoselectivity Synthesis (chemical) Asymmetric allylic alkylations Asymmetric synthesis Chiral pyridines Oxazolines Relay catalysis Relay system Ru catalysts Stereocenters Tetra-hydrofuran Tetrahydrofurans
URL	查看原文
收录类别	SCI ; EI
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:001477007500001
出版者	AMER CHEMICAL SOC
EI入藏号	20251818328805
EI主题词	Catalysis
EI分类号	801 Chemistry ; 801.1 Biochemistry ; 802.2 Chemical Reactions ; 804 Chemical Products
原始文献类型	Journal article (JA)
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/527133
专题	物质科学与技术学院物质科学与技术学院_硕士生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_叶柏华组
共同第一作者	Liu, Fang-Jie
通讯作者	Ye, Baihua
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	Li, Xuejiao,Liu, Fang-Jie,Ye, Baihua. Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by Rh^II/Ru^II Relay Catalysis[J]. JOURNAL OF ORGANIC CHEMISTRY,2025.
APA	Li, Xuejiao,Liu, Fang-Jie,&Ye, Baihua.(2025).Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by Rh^II/Ru^II Relay Catalysis.JOURNAL OF ORGANIC CHEMISTRY.
MLA	Li, Xuejiao,et al."Asymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by Rh^II/Ru^II Relay Catalysis".JOURNAL OF ORGANIC CHEMISTRY (2025).