机构：[1]College of Chemistry, Fuzhou University, Fuzhou 350116, China.[2]State Key Laboratory of Structural Chemistry and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.[3]Orthopedics Department, Guangdong Provincial Hospital of Traditional Chinese Medicine, The Second Affiliated Hospital of Guangzhou University of Chinese Medicine, Guangzhou 510120, China.广东省中医院[4]Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Department of Chemistry, Jinan University, Guangzhou 510632, China.
The Nazarov cyclization has been established as a powerful tool in constructing cyclopentenone skeletons. In sharp contrast, oxa-Nazarov cyclization that affords dihydrofuranones, a new type of product, has been less explored. In this work, we report the I2-catalyzed oxa-Nazarov cyclization-Michael addition cascade between vinyl α-diketones and enones. The protocol allows access to a range of functionalized dihydrofuranones with good to high yields, and diverse further transformations on the products have been achieved. Furthermore, the mechanistic studies reveal that the 1,2-hydride shift occurs simultaneously during the dihydrofuranone formation.
基金：
National Natural Science
Foundation of China (Nos. 22071242, 22173083, 21871260),
the Strategic Priority Research Program of the Chinese
Academy of Sciences (No. XDB20000000), Fujian Natural
Science Foundation (No. 2021J01522), Open Fund of
Guangdong Provincial Key Laboratory of Functional Supramolecular
Coordination Materials and Applications (No.
2020B08), and the Fundamental Research Funds (No.
11620416 and No. 202201020559).
第一作者机构：[1]College of Chemistry, Fuzhou University, Fuzhou 350116, China.
共同第一作者：
通讯作者：
通讯机构：[1]College of Chemistry, Fuzhou University, Fuzhou 350116, China.[2]State Key Laboratory of Structural Chemistry and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.[3]Orthopedics Department, Guangdong Provincial Hospital of Traditional Chinese Medicine, The Second Affiliated Hospital of Guangzhou University of Chinese Medicine, Guangzhou 510120, China.[4]Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Department of Chemistry, Jinan University, Guangzhou 510632, China.[*1]College of Chemistry, Fuzhou University, Fuzhou 350116, China[*2]State Key Laboratory of Structural Chemistry and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China[*3]Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Department of Chemistry, Jinan University, Guangzhou 510632, China[*4]Orthopedics Department, Guangdong Provincial Hospital of Traditional Chinese Medicine, The Second Affiliated Hospital of Guangzhou University of Chinese Medicine, Guangzhou 510120, China
推荐引用方式(GB/T 7714)：
Chen Ting,Gong Fan,Nagaraju Sakkani,et al.Oxa-Nazarov Cyclization-Michael Addition Sequence for the Rapid Construction of Dihydrofuranones[J].ORGANIC LETTERS.2022,24(48):8837-8842.doi:10.1021/acs.orglett.2c03601.
APA：
Chen Ting,Gong Fan,Nagaraju Sakkani,Liu Jinggong,Yang Shuang...&Fang Xinqiang.(2022).Oxa-Nazarov Cyclization-Michael Addition Sequence for the Rapid Construction of Dihydrofuranones.ORGANIC LETTERS,24,(48)
MLA：
Chen Ting,et al."Oxa-Nazarov Cyclization-Michael Addition Sequence for the Rapid Construction of Dihydrofuranones".ORGANIC LETTERS 24..48(2022):8837-8842
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