高等学校化学学报 ›› 2001, Vol. 22 ›› Issue (10): 1677.

• 研究论文 • 上一篇    下一篇

手性膦酸二酯类化合物的合成与结构

李学强, 陈庆华   

  1. 北京师范大学化学系, 北京 100875
  • 收稿日期:2000-08-29 出版日期:2001-10-24 发布日期:2001-10-24
  • 通讯作者: 陈庆华(1935年出生),男,教授,博士生导师,主要从事不对称合成及环加成反应的研究.*现在宁夏大学化学系.
  • 基金资助:

    国家自然科学基金(批准号:29672004)资助

Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives

LI Xue-Qiang, CHEN Qinq-Hua   

  1. Department of Chemistry, Beijing Normal University, Beijing 100875, China
  • Received:2000-08-29 Online:2001-10-24 Published:2001-10-24

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.

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

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.

Key words: New chiral phosphonate reagent, Tandem asymmetric Michael addition/Intromolecular Michalis Arbazov rearangement reaction, Crystal structure, 5 (1 S ) Bornyloxy4 dialkyloxyphosphonyl3 halo2(5H) furanone

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