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Rhodium(Ⅲ)-catalyzed diastereo-and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tetheredα,β-unsaturated aldehydes

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Chinese Chemical Letters 2024年第9期35卷 160-164页

作者： Yi-Fan Wang Hao-Yun Yu Hao Xu Ya-Jie Wang Xiaodi Yang Yu-Hui Wang Ping Tian Guo-Qiang Lin The Research Center of Chiral Drugs Shanghai Frontiers Science Center for TCM Chemical BiologyInnovation Research Institute of Traditional Chinese MedicineShanghai University of Traditional Chinese MedicineShanghai 201203China

A rhodium(Ⅲ)-catalyzed hydrosilylation/cyclization reaction of cyclohexadienone-tetheredα,β-unsaturated aldehydes(1,6-dienes)with triethylsilane is described,providing a series of cishydrobenzofurans,cis-hydroindoles,and cishydroindenes bearing silyl enol ether in good to excellent yields and excellent ***,the versatility of this method was demonstrated through a gram-scale experiment and various downstream transformations,highlighting its utility.

关键词： Rhodium(Ⅲ)catalysis Hydrosilylation/cyclization 1,6-Dienes silyl enol ether Diastereo-and enantioselectivity

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Visible Light-Induced Methoxycarbonyldifluoromethylation of Trime-thylsilyl enol ethers and Allyltrimethylsilanes with FSO2CF2CO2Me

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Chinese Journal of Chemistry 2018年第11期36卷 1024-1030页

作者： Wei Yu Yao Ouyang Xiu-Hua Xu Feng-Ling qing Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecules Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Science 345 Lingling Lu Shanghai 200032 China Key Laboratory of Science and Technology of Eco-Textiles Ministry of Education College of Chemistry Chemical Engineering and Biotechnolo- gy Donghua University 2999 North Renmin Lu Shanghai 202620 China

A photocatalytic methoxycarbonyldifluoromethylation of trimethylsilyl enol ethers with FSO2CF2CO2Me in the presence of fac‐Ir(ppy)3 was developed. This reaction provided a practical strategy for the construction of various α‐CF2CO2R aromatic ketones, which are difficult to access by other methods. Furthermore, a series of methoxycarbonyldifluoromethylated allylic compounds could also be obtained from allyltrimethylsilanes using the same strategy. The resulting CF2CO2R‐containing products are useful building blocks and potentially valuable in medicinal chemistry and material sciences.

关键词： methoxycarbonyldifluoromethylation silyl enol ether allylsilane ketones allylic compounds radical reactions

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Synthesis of 14-Bromo and 14-Hydroxy Baccatin III Derviatives

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Chinese Chemical Letters 2001年第8期12卷 675-678页

作者： Wei Shuo FANG Qi Cheng FANG Xiao Tian LIANG Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College1 Xian Nong Tan StreetBeijing 100050

Several 14 alpha- and 14 beta -bromo baccatin III derivatives were synthesized by direct bromination and from silyl enol ether of 13-oxo-7-TES-baccatin III. 14 beta -Hyroxy baccatin III derivative was also obtained fr... 详细信息

关键词： Bromo baccatin III 14-hydroxy baccatin III paclitaxel silyl enol ether

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Chiral nickel(Ⅱ) complex catalyzed asymmetric(3+2) cycloaddition ofα-diazo pyrazoleamides with 2-siloxy-1-alkenes

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Chinese Chemical Letters 2023年第4期34卷 322-325页

作者： Wei Yang Zhendong Yang Long Chen Yican Lu Cefei Zhang Zhishan Su Xiaohua Liu Xiaoming Feng Key Laboratory of Green Chemistry&Technology Ministry of EducationCollege of ChemistrySichuan UniversityChengdu 610064China

A highly efficient asymmetric(3 + 2) cycloaddition of α-diazo pyrazoleamides with silyl enol ethers was realized by employing a chiral N,N’-dioxide-Ni(II) complex catalyst. The process includes the formation of chiral nickel carbenoid intermediate and the following enantioselective cycloaddition reaction. The desired dihydrofuran O,O-acetal derivatives were obtained in good yields(up to 90%) with high enantioselectivity(up to 99% ee) under mild reaction conditions within short reaction time. On the basis of the determination of the catalyst structure, a possible transition state mode was proposed.

关键词： Asymmetric catalysis (3+2)Cycloaddition Chiral N,N’-dioxide silyl enol ether α-Diazo pyrazoleamide Dihydrofuran

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