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MgO-Promoted [4+2] Cyclization Using HFA?3H2O/SOCl2/PPh3: Modular Synthesis of gem-Bis(trifluoromethyl)dihydrothiopyrans  ( SCI-EXPANDED收录)  

文献类型:期刊文献

英文题名:MgO-Promoted [4+2] Cyclization Using HFA?3H2O/SOCl2/PPh3: Modular Synthesis of gem-Bis(trifluoromethyl)dihydrothiopyrans

作者:Zeng, Zhengwu Rao, Junyi Pei, Meng Xiang, Lu Sun, Yameng Shen, Yongcun Chen, Zhenling Jiang, Zhong-Xing Yang, Zhigang

第一作者:Zeng, Zhengwu

通信作者:Yang, ZG[1]

机构:[1]Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Wuhan 430070, Peoples R China;[2]Wuhan Univ, Zhongnan Hosp, Sch Pharmaceut Sci, Dept Spine Surg & Musculoskeletal Tumor, Wuhan 430071, Peoples R China;[3]Guizhou Inst Technol, Sch Chem Engn, Guiyang 550003, Peoples R China;[4]Chinese Acad Sci, Wuhan Inst Phys & Math, Innovat Acad Precis Measurement Sci & Technol, Natl Ctr Magnet Resonance Wuhan,State Key Lab Magn, Wuhan 430071, Peoples R China

第一机构:Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Wuhan 430070, Peoples R China

通信机构:corresponding author), Wuhan Univ, Zhongnan Hosp, Sch Pharmaceut Sci, Dept Spine Surg & Musculoskeletal Tumor, Wuhan 430071, Peoples R China.

年份:2026

外文期刊名:ORGANIC LETTERS

收录:;WOS:【SCI-EXPANDED(收录号:WOS:001830238400001)】;

基金:This research was supported by the Chinese Medicine Scientific Research Projects of Hubei Provincial Administration of Traditional Chinese Medicine (ZY2025M041), the Hubei Province Health and Family Planning Scientific Research Project (WJ2025M199), the High Level Scientific Research Funding Project of Guizhou Institute of Technology (2023GCC024), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB0540000), the National Natural Science Foundation of China (22327901), the Science and Technology Plan Project of Guizhou Province (QiankeheJichu ZK[2024] yiban 519, ZK [2023] yiban 132), the Youth Science and Technology Talent Growth Project of Education Department of Guizhou Province (Qian Jiao Ji (2024)172), and the Translational Medicine and Interdisciplinary Research Joint Fund of Zhongnan Hospital of Wuhan University (ZNJC202327). We thank Mr Ran Zhang from the Core Facility of Wuhan University for his assistance with NMR analysis.

语种:英文

摘要:The present study reports an unprecedented [4 + 2] annulation for the modular synthesis of gem-bis(trifluoromethyl)-3,6-dihydro-2H-thiopyrans. The transformation employs readily available HFA & centerdot;3H(2)O and SOCl2 as a convenient (CF3)(2)C=S surrogate in the presence of PPh3, with MgO promoting the subsequent thia-Diels-Alder reaction of 1,3-dienes. The method features a broad substrate scope, excellent practicality for gram-scale synthesis and late-stage functionalization of biologically active molecules, as well as versatile product derivatization. Mechanistic studies identify hexafluoroisopropyl polysulfide species as key intermediates in this process.

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