| Catalytic Enantioselective Protonation of Monofluorinated Silyl Enol Ethers towards Chiral α-Fluoroketones |
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| 引用本文： | Kui Liao,Xiao-Si Hu,Ren-Yi Zhu,Ruo-Han Rao,Jin-Sheng Yu,Feng Zhou,Jian Zhou. Catalytic Enantioselective Protonation of Monofluorinated Silyl Enol Ethers towards Chiral α-Fluoroketones[J]. 中国化学, 2019, 37(8): 799-806. DOI: 10.1002/cjoc.201900198 |
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| 作者姓名： | Kui Liao Xiao-Si Hu Ren-Yi Zhu Ruo-Han Rao Jin-Sheng Yu Feng Zhou Jian Zhou |
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| 作者单位： | Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development/Shanghai Key Laboratory of Green Chemistry and Chemical Processes;Chengdu Shude High School Foreign Language Campus;State Key Laboratory of Organometallic Chemistry |
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| 基金项目： | support from the National Natural Science Foundation of China (No.21725203). |
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| 摘 要： | Summary of main observation and conclusion Described herein is an organocatalytic enantioselective protonation of monofluorinated silyl enol ethers,affording an array of optically active α-secondary α-fluoroketones in good to high yields and enantioselectivities,under the catalysis of bifunctional cinchonidine derived squaramide C4.It represents a rare example of facile synthesis of enantioenriched α-secondary α-fluoroketones.With D20 as the deuterium source and MeOD as the solvent,the first highly enantioselective preparation of chiral α-deuterated α-fluoroketones in >92% deuteration is developed.
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| 关 键 词： | IS |
Catalytic Enantioselective Protonation of Monofluorinated Silyl Enol Ethers towards Chiral α‐Fluoroketones |
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| Kui Liao,Xiao‐Si Hu,Ren‐Yi Zhu,Ruo‐Han Rao,Jin‐Sheng Yu,Feng Zhou,Jian Zhou. Catalytic Enantioselective Protonation of Monofluorinated Silyl Enol Ethers towards Chiral α‐Fluoroketones[J]. Chinese Journal of Chemistry, 2019, 37(8): 799-806. DOI: 10.1002/cjoc.201900198 |
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| Authors: | Kui Liao Xiao‐Si Hu Ren‐Yi Zhu Ruo‐Han Rao Jin‐Sheng Yu Feng Zhou Jian Zhou |
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| Abstract: | Described herein is an organocatalytic enantioselective protonation of monofluorinated silyl enol ethers, affording an array of optically active α‐secondary α‐fluoroketones in good to high yields and enantioselectivities, under the catalysis of bifunctional cinchonidine derived squaramide C4 . It represents a rare example of facile synthesis of enantioenriched α‐secondary α‐fluoroketones. With D2O as the deuterium source and MeOD as the solvent, the first highly enantioselective preparation of chiral α‐deuterated α‐fluoroketones in >92% deuteration is developed. |
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