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| Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones | |
| 作者姓名： | CAO Long ;ZHOU Xiaohong ;CHEN Jie ;ZHANG Hui ;DENG Hongmei ;SHAO Min ;McMILLS Mark C. ;CAO Weiguo |
| 作者单位： | [1]Department of Chemistry, Shanghai University, Shanghai 200444, P. R. China; [2]State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China; [3]Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. China; [4]Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA |
| 基金项目： | Supported by the National Natural Science Foundation of China（No.21272152）. |
| 摘 要： | Trans-2,3-dihydrofuran derivatives 3 or 4 substituted with a sulfonyl group were prepared with high chemoselectivity and good yields by 1＋4]-addition reaction of α,β-unsaturated ketones 1 with arsonium bromide 2 in CH2Cl2 in the presence of potassium carbonate at room temperature.The structures of the products were characterized by IR,MS,^1H NMR,elemental analysis and single crystal X-ray diffraction analysis.A mechanism for the formation of products was also proposed. |
| 关 键 词： | 呋喃衍生物 不饱和酮 酰基取代 二氢呋喃 立体选择性合成 胂叶立德 反式 反应 |
Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones |
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| CAO Long,;ZHOU Xiaohong,;CHEN Jie,;ZHANG Hui,;DENG Hongmei,;SHAO Min,;McMILLS Mark C.,;CAO Weiguo.Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones[J].Chemical Research in Chinese University,2014,30(4):596-600. | |
| Authors: | CAO Long ZHOU Xiaohong CHEN Jie ZHANG Hui DENG Hongmei SHAO Min McMILLS Mark C CAO Weiguo |
| Institution: | 1. Department of Chemistry, Shanghai University, Shanghai 200444, P. R. China; 2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China; 3. Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. China; 4. Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA |
| Abstract: | Trans-2,3-dihydrofuran derivatives 3 or 4 substituted with a sulfonyl group were prepared with high chemoselectivity and good yields by 1+4]-addition reaction of α,β-unsaturated ketones 1 with arsonium bromide 2 in CH2Cl2 in the presence of potassium carbonate at room temperature. The structures of the products were characterized by IR, MS, 1H NMR, elemental analysis and single crystal X-ray diffraction analysis. A mechanism for the formation of products was also proposed. |
| Keywords: | Stereoselectivity Dihydrofuran Arsonium Ylide |
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