| An Efficient Synthesis of Highly Optically Active 4-Substituted-2（5H）-furanones from Chiral 3-Bromo-2（5H）-furanone |
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| 引用本文： | 范雪娥,黄敏,黄慧,陈庆华.An Efficient Synthesis of Highly Optically Active 4-Substituted-2（5H）-furanones from Chiral 3-Bromo-2（5H）-furanone[J].中国化学,2004,22(11):1359-1365. |
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| 作者姓名： | 范雪娥 黄敏 黄慧 陈庆华 |
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| 作者单位： | [1]DepartmentofChemistry,LuoyangNormalCollege,Luoyang,Henan471022,China [2]DepartmentofChemistry,BeijingNormalUniversity,Beijing100875,China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China (No. 29672004). |
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| 摘 要： | Highly optically active 4-substituted-2(5H)-furanones 6a-6j were obtained in good yields with de≥98% by the tandem Michael addition/elimination reaction of chiral 3-bromo-2(SH)-furanone (4a), which was conveniently prepared starting from 2-furaldehyde under mild conditions. The products were identified on the basis of their satisfactory elemental analysis and spectroscopic data of IR, UV, ^1H NMR, ^13C NMR and mass spectra. The stereochemistry and absolute configuration of this type of compounds were established by the X-ray crystallographic study. The reaction provided a short and efficient synthesis of the interesting highly optically active 4-subsdtuted-2(5H)-furanones containing an active pyrimidine and a purine base group.
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| 关 键 词： | 合成 4-取代-2（5H）-呋喃酮 光学活性 3-溴-2（5H）-呋喃酮 2-糠醛 X射线晶体学 迈克尔加成反应 消去反应 嘧啶 嘌呤 |
An Efficient Synthesis of Highly Optically Active 4-Substituted- 2(5H)-furanones from Chiral 3-Bromo-2(5H)-furanone |
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| Xue‐E Fan,Min Huang,Hui Huang,Qing‐Hua Chen.An Efficient Synthesis of Highly Optically Active 4-Substituted- 2(5H)-furanones from Chiral 3-Bromo-2(5H)-furanone[J].Chinese Journal of Chemistry,2004,22(11):1359-1365. |
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| Authors: | Xue‐E Fan Min Huang Hui Huang Qing‐Hua Chen |
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| Institution: | FAN,Xue-Ea HUANG,Minb,? HUANG,Huib,CHEN,Qing-Hua*,a,b a Department of Chemistry,Luoyang Normal College,Luoyang,Henan 471022,China b Department of Chemistry,Beijing Normal University,Beijing 100875,China |
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| Abstract: | Highly optically active 4‐substituted‐2(5H)‐furanones 6a‐6j were obtained in good yields with de?98% by the tandem Michael addition/elimination reaction of chiral 3‐bromo‐2(5H)‐furanone (4a), which was conveniently prepared starting from 2‐furaldehyde under mild conditions. The products were identified on the basis of their satisfactory elemental analysis and spectroscopic data of IR, W, 1H NMR, 13C NMR and mass spectra. The stereochemistry and absolute configuration of this type of compounds were established by the X‐ray crystallographic study. The reaction provided a short and efficient synthesis of the interesting highly optically active 4‐substituted‐2(5H)‐furanones containing an active pyrimidine and a purine base group. |
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| Keywords: | optically active 4-substituted-2(5H)-furanone tandem asymmetric Michael addition/elimination re-action pyrimidine or purine base group X-ray crystallography |
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