Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (9): 1295-1299. Previous Articles     Next Articles

Reports

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

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