| Synthesis of 5-Fluoroalkyl Isoxazolidines via 1,3-Dipolar Cycloaddition of Ethyl 2-Hydropolyfluoroalk-2-enoates with Nitrones |
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| 引用本文： | 刘金涛 金其辉 吕贺军 黄维垣. Synthesis of 5-Fluoroalkyl Isoxazolidines via 1,3-Dipolar Cycloaddition of Ethyl 2-Hydropolyfluoroalk-2-enoates with Nitrones[J]. 中国化学, 2004, 22(9): 945-949. DOI: 10.1002/cjoc.20040220914 |
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| 作者姓名： | 刘金涛 金其辉 吕贺军 黄维垣 |
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| 作者单位： | KeyLaboratoryofOrganofluorineChemistry,ShanghaiInstituteofOrganicChemistry,ChineseAcademyofSciences,Shanghai200032,China |
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| 基金项目： | the National Natural Science Foundation of China (No. 20172065). |
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| 摘 要： | 1,3-Dipolar cycloaddition reactions of ethyl 2-hydropolyfluoroalk-2-enoates (1) with some nitrones were described. The reaction of 3,4-dihydroisoquinoline N-oxide (2) with 1 took place readily in methylene chloride at room temperature to give the corresponding 5-fluoroalkylisoxazolidines regioselectively as a mixture of two diastereoisomers (trans and cis) in high yields, while longer reaction time and higher temperature were needed in the case of non-cyclic nitrones. Under similar conditions the reaction of quinoline N-oxide (14) with 1 did not give the expected adducts and a ring-opening product was obtained.
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| 关 键 词： | 合成 5-氟烷基异唑酮 1 3-二极性环加成 乙基2-氢化聚氟代碱-2甲基丙烯酸 硝基酮 |
Synthesis of 5-Fluoroalkyl Isoxazolidines via 1,3-Dipolar Cycloaddition of Ethyl 2-Hydropolyfluoroalk-2- enoates with Nitrones |
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| LIU,Jin-Tao JIN,Qi-Hui L He-Jun HUANG,Wei-Yuan Key Laboratory of Organofluorine Chemistry. Synthesis of 5-Fluoroalkyl Isoxazolidines via 1,3-Dipolar Cycloaddition of Ethyl 2-Hydropolyfluoroalk-2- enoates with Nitrones[J]. Chinese Journal of Chemistry, 2004, 22(9): 945-949. DOI: 10.1002/cjoc.20040220914 |
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| Authors: | LIU Jin-Tao JIN Qi-Hui L He-Jun HUANG Wei-Yuan Key Laboratory of Organofluorine Chemistry |
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| Affiliation: | LIU,Jin-Tao JIN,Qi-Hui L He-Jun HUANG,Wei-Yuan Key Laboratory of Organofluorine Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China |
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| Abstract: | Dipolar cycloaddition reactions of ethyl 2-hydropolyfluoroalk-2-enoates (1) with some nitrones were de-scribed. The reaction of 3,4-dihydroisoquinoline N-oxide (2) with 1 took place readily in methylene chloride at room temperature to give the corresponding 5-fluoroalkylisoxazolidines regioselectively as a mixture of two di-astereoisomers (trans and cis) in high yields, while longer reaction time and higher temperature were needed in the case of non-cyclic nitrones. Under similar conditions the reaction of quinoline N-oxide (14) with 1 did not give the expected adducts and a ring-opening product was obtained. |
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| Keywords: | fluoroalkyl isoxazolidine ethyl 2-hydropolyfluoroalk-2-enoate nitrone cycloaddition synthesis |
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