| (5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮与氨基酸的串联反应 |
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| 引用本文： | 谭越河,汪朝阳,郝志峰,李建晓. (5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮与氨基酸的串联反应[J]. 有机化学, 2011, 31(8) |
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| 作者姓名： | 谭越河 汪朝阳 郝志峰 李建晓 |
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| 作者单位： | 1. 华南师范大学化学与环境学院 广州510006
2. 广东工业大学轻工化工学院 广州510006 |
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| 基金项目： | 国家自然科学基金(No.20772035); 广东省自然科学基金(No.5300082)资助项目 |
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| 摘 要： | 在氢氧化钾作用下,直接以不同种类氨基酸为亲核试剂,与手性(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮在室温下进行串联的不对称迈克尔加成-消除反应,合成了15个新的光学活性2(5H)-呋喃酮衍生物.通过旋光度,UV-Vis,IR,1H NMR,13C NMR,MS,元素分析和X射线单晶衍射等表征方法,确定了目标化合物的化学结构和绝对构型.
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| 关 键 词： | (5S)-5-烷氧基-3 4-二卤-2(5H)-呋喃酮 氨基酸 串联迈克尔加成-消除反应 光学活性 多手性中心 |
Tandem Reaction of(5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids |
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| Tan Yuehe,Wang Zhaoyang,Hao Zhifeng,Li Jianxiao. Tandem Reaction of(5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids[J]. Chinese Journal of Organic Chemistry, 2011, 31(8) |
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| Authors: | Tan Yuehe Wang Zhaoyang Hao Zhifeng Li Jianxiao |
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| Affiliation: | Tan,Yuehea Wang,Zhaoyang*,a Hao,Zhifengb Li,Jianxiaoa(a School of Chemistry and Environment,South China Normal University,Guangzhou 510006)(b Faculty of Chemical Engineering and Light Industry,Guangdong University of Technology,Guangzhou 510006) |
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| Abstract: | Different kinds of amino acids,directly serving as nucleophiles,were reacted with(5S)-5-alkoxy-3,4-dihalo-5H-furan-2-ones via tandem asymmetric Michael addition-elimination in the presence of potassium hydroxide to give 15 new optically active 5H-furan-2-one derivatives.The chemical structures and absolute configurations of these compounds were confirmed via rotation,UV-Vis,IR,1H NMR,13C NMR,MS,elemental analysis and X-ray single crystal diffraction. |
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| Keywords: | (5S)-5-alkoxy-3 4-dihalo-5H-furan-2-one amino acid tandem Michael addition-elimination optical activity multiple chiral center |
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