| 手性膦酸二酯类化合物的合成与结构 |
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| 引用本文： | 李学强,陈庆华.手性膦酸二酯类化合物的合成与结构[J].高等学校化学学报,2001,22(10):1677-1681. |
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| 作者姓名： | 李学强 陈庆华 |
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| 作者单位： | 北京师范大学化学系, 北京 100875 |
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| 基金项目： | 国家自然科学基金 (批准号 :2 96 72 0 0 4)资助 |
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| 摘 要： | 手性呋喃酮1a1b与亚磷酸三酯2a2b通过串联的不对称Michael加成/分子内Michalis-Arbazov重排反应,得到含磷官能团的新手性化合物5-(S)-(1S)-冰片氧基-4-膦酸二酯基-3-卤素-2(5H)-呋喃酮(3a～3d).该反应具有条件温和,产率高(69%～93%),光学纯度单一(d.e.≥98%)等特点.通过元素分析,IR,UV1HNMR13CNMR,MS,α]D20等分析数据以及X射线四圆衍射确定了它们的化学结构和绝对构型.
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| 关 键 词： | 新手性磷试剂 串联的不对称Michael加成/分子内Michalis-Arbazov重排反应 晶体结构 手性4-膦酸二酯基-3-卤-2-(5H)呋喃酮 |
| 文章编号： | 0251-0790(2001)10-1677-05 |
| 收稿时间： | 2000-08-29 |
Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives |
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| LI Xue-Qiang,CHEN Qinq-Hua.Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives[J].Chemical Research In Chinese Universities,2001,22(10):1677-1681. |
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| Authors: | LI Xue-Qiang CHEN Qinq-Hua |
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| Institution: | Department of Chemistry, Beijing Normal University, Beijing 100875, China |
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| Abstract: | The tandem asymmetric Michael addition/internal Michalis Arbazov reaction of compound 1 with nucleophilic trialkylphosphites has been investigated. The asymmetric reaction afforded optically pure-5-(1S) bornyloxy-4-dialkyloxy phosphonyl-3-halo-2(5H) furanones 3a_3d at a mild condition in 69%-95% yield with d.e.≥98%. The chemical structure and configuration of the chiral compounds 3a3d were identified on the basis of their elemental analytical data and spectroscopic data, such as α]D20 , UV, IR, 1H NMR, 13C NMR, MSand Xray crystallography. |
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| Keywords: | New chiral phosphonate reagent Tandem asymmetric Michael addition/Intromolecular Michalis Arbazov rearangement reaction Crystal structure 5 (1 S ) Bornyloxy 4 dialkyloxyphosphonyl 3 halo 2(5H) furanone |
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