| Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed“interrupted”Feist-Bénary reaction |
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| 作者姓名： | Hui Chen Ru Jiang Qiao Feng Wang Xiao Li Sun Jing Luo Sheng Yong Zhang |
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| 作者单位： | a Department of Chemistry, Fourth Military Medical University, Xi'an 710032, China;b Department of Shannxi Institute for Food and Drug Control, Xi'an 710061, China |
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| 基金项目： | the National Natural Science Foundation of China(Nos.20572131,20372083,20972189,20672141, 30901883) |
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| 摘 要： | <正>In this study,six thiourea derivatives of cinchona alkaloids with 9-nat or 9-epi-configuration were synthesized.After characterized the structures,we adopted them to the asymmetric"interrupted"Feist-Benary(IFB) reaction ofα-haloketones with β-dicarbonyl compounds,to give optically active dihydrofurans.Various thiourea derivatives as organocatalysts were examined.The corresponding chiral hydroxyl dihydrofurans have been obtained in excellent yields and moderate ees.To the acyclic substrate,we obtained exciting and promising result.
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| 关 键 词： | "Interrupted" Feist-Bé nary (IFB) reaction Chital Thiourea Dihydrofuran |
| 收稿时间： | 25 June 2009 |
Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction |
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| Hui Chen,Ru Jiang,Qiao Feng Wang,Xiao Li Sun,Jing Luo,Sheng Yong Zhang.Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction[J].Chinese Chemical Letters,2010,21(2):167-170. |
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| Authors: | Hui Chen Ru Jiang Qiao Feng Wang Xiao Li Sun Jing Luo Sheng Yong Zhang |
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| Institution: | a Department of Chemistry, Fourth Military Medical University, Xi'an 710032, China;b Department of Shannxi Institute for Food and Drug Control, Xi'an 710061, China |
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| Abstract: | In this study, six thiourea derivatives of cinchona alkaloids with 9-nat or 9-epi configuration were synthesized. After characterized the structures, we adopted them to the asymmetric “interrupted” Feist-Bénary (IFB) reaction of α-haloketones with β-dicarbonyl compounds, to give optically active dihydrofurans. Various thiourea derivatives as organocatalysts were examined. The corresponding chiral hydroxyl dihydrofurans have been obtained in excellent yields and moderate ees. To the acyclic substrate, we obtained exciting and promising result. |
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| Keywords: | Chital Thiourea Dihydrofuran |
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