Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2423-2429.DOI: 10.6023/cjoc201703018 Previous Articles     Next Articles



李伟东a, 韩生华b, 刘艳红a, 陈建新a   

  1. a 山西师范大学化学与材料科学学院 临汾 041004;
    b 山西大同大学化学与工程学院 大同 037009
  • 收稿日期:2017-03-08 修回日期:2017-04-17 发布日期:2017-05-17
  • 通讯作者: 陈建新
  • 基金资助:


Synthesis of α-Alkoxycarbonyl-α-siloxyamides by the Reaction of a Carbamoylsilane with α-Ketoesters

Li Weidonga, Han Shenghuab, Lui Yanhonga, Chen Jianxina   

  1. a College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004;
    b College of Chemistry and Engineering, Shanxi Datong University, Datong 037009
  • Received:2017-03-08 Revised:2017-04-17 Published:2017-05-17
  • Contact: 10.6023/cjoc201703018
  • Supported by:

    Project supported by the Shanxi Province Foundation for Returness Overseas Scientists (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of the Modern College of Arts and Science, Shanxi Normal University (No. WL2016CXCY-YJ-30).

N,N-Dimethylcarbamoyl(trimethyl)silane reacted with a series of α-ketoesters in anhydrous toluene at 60℃ to afford α-alkoxycarbonyl-α-siloxy amide derivatives in good yields (70%~99%). When the alkyl of α-ketoesters was L-2-isopropyl-5-methylcyclohexyl, the reactions possess stereo selectivity. The experimental results showed that the electronic property of the substituted group on the aryl ring affected both the reaction ratio and the yields of products. The structures of the products were characterized by element analysis, 1H NMR, 13C NMR and IR spectra. A reaction mechanism is proposed. The mild and no catalyst conditions, simple procedure, less byproducts and good yields provide an effective method for the preparation of α-alkoxycarbonyl-α-hydroxy amides.

Key words: carbamoylsilane, α-ketoesters, α-alkoxycarbonyl-α-hydroxyamides, nucleophilic addition, synthetic methods