| Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1-Cyanoethyl)phosphonates. Synthesis of Perfluoroalkylated α,β-Unsaturated Nitriles with Predominant Z-Selectivity |
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| 引用本文： | 沈延昌
,江国防.Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1-Cyanoethyl)phosphonates. Synthesis of Perfluoroalkylated α,β-Unsaturated Nitriles with Predominant Z-Selectivity[J].中国化学,2002,20(11):1375-1378. |
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| 作者姓名： | 沈延昌 江国防 |
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| 作者单位： | SHEN，Yan-Chang JIANG，Guo-FangState Key Laboratory of Organometallic Chemistry，Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences，Shanghai 200032，China |
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| 基金项目： | theNationalNaturalScienceFoundationofChina (No.2 9972 0 46 )andChineseAcademyofSciences |
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| 摘 要： | ＩｎｔｒｏｄｕｃｔｉｏｎＲｅｃｅｎｔｌｙｍｕｃｈａｔｔｅｎｔｉｏｎｈａｓｂｅｅｎｄｅｖｏｔｅｄｔｏｔｈｅｓｙｎｔｈｅｓｉｓｏｆα ,β ｕｎｓａｔｕｒａｔｅｄｎｉｔｒｉｌｅｓｓｉｎｃｅｔｈｅｙａｒｅｉｍ ｐｏｒｔａｎｔｓｔｒｕｃｔｕｒａｌｆｅａｔｕｒｅｏｆｓｅｖｅｒａｌｎａｔｕｒａｌｌｙｏｃｃｕｒｒｉｎｇｂｉ ｏｌｏｇｉｃａｌｌｙａｃｔｉｖｅｃｏｍｐｏｕｎｄｓ .1,2 Ｔｈｅｉｎｔｒｏｄｕｃｔｉｏｎｏｆｆｌｕｏ ｒｉｎｅｏｒｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌｇｒｏｕｐｉｎｔｏｂｉｏｌｏｇｉｃａｌｌｙａｃｔｉｖ…
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| 关 键 词： | perfluoroalkylated α β-unsaturated nitrile Grignard reagent diethyl (1-cyanoethyl)phosphonate Z-selectivity |
Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1‐Cyanoethyl) phosphonates. Synthesis of Perfluoroalkylated α, β‐Unsaturated Nitriles with Predominant Z‐Selectivity |
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| SHEN,Yan-Chang JIANG,Guo-FangState Key Laboratory of Organometallic Chemistry.Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1‐Cyanoethyl) phosphonates. Synthesis of Perfluoroalkylated α, β‐Unsaturated Nitriles with Predominant Z‐Selectivity[J].Chinese Journal of Chemistry,2002,20(11):1375-1378. |
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| Authors: | SHEN Yan-Chang JIANG Guo-FangState Key Laboratory of Organometallic Chemistry |
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| Institution: | SHEN,Yan-Chang JIANG,Guo-FangState Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China |
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| Abstract: | Diethyl (1‐cyanoethyl) phosphorate 1 was reacted with n‐butyl‐lithium in tetrahydrofuran (THF) at ‐ 78 °C and the resulting carbanion 2 reacted with perfluoroalkanoic add anhydride to afford perfluoroacylated phosphorate 3. Without isolation 3 was attacked by Grignard reagents giving perfluoroalkylated α, β‐unsaturated nitriles in 46%‐88% yields with high Z‐stereoselectivity (Z: E = 89–62:11–38). |
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| Keywords: | perfluoroalkylated α β‐unsaturated nitrile Grignard reagent diethyl (l‐cyanoethyl)phosphonate Z‐selectivity |
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