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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (9): 1295-1299. 上一篇    下一篇

研究简报

由硅醚经脱保护-氧化-Wittig反应一锅法合成α,β-不饱和酯

邓桂胜*，许百华，刘春玉   

  1. (湖南师范大学化学化工学院 长沙 410081)
  • 收稿日期:2005-11-26 修回日期:2006-02-20 发布日期:2006-09-11
  • 通讯作者: 邓桂胜

One-Pot Synthesis of α,β-Unsaturated Esters from Silyl Ethers by Means of in situ Deprotection-Oxidation-Wittig Re-action

DENG Gui-Sheng*,XU Bai-Hua,LIU Chun-Yu   

  1. (College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081)
  • Received:2005-11-26 Revised:2006-02-20 Published:2006-09-11
  • Contact: DENG Gui-Sheng

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在1摩尔醋酸和稳定的Wittig试剂存在下, 活性MnO2作为氧化剂时, 硅醚发生脱保护-氧化-Wittig反应. 考查了各种硅醚, 诸如苄基硅醚、炔丙基硅醚、烯丙基硅醚和烷基硅醚等作底物在反应性能方面的差异. 该反应使硅醚直接形成碳碳双键而得到α,β-不饱和酯. 产物的结构经红外光谱、核磁共振谱表征.

关键词: 硅醚, Wittig反应, 二氧化锰, ,-不饱和酯

The in situ silylzed ether deprotection-oxidation-Wittig reaction using manganese dioxide as the oxidant in the presence of one equivalent of acetic acid and stable phosphoranes has been applied to various silyl ethers such as benzylic, propargylic, allylic and alkylic silyl ethers. The reaction results in the direct carbon-carbon double bond formation from silyl ethers to give the corresponding α,β-unsaturated esters. The structures of the products were confirmed by IR and 1H NMR spectra.

Key words: silyl ether, Wittig reaction, manganese dioxide, α,β-unsaturated ester