Chem. J. Chinese Universities ›› 2011, Vol. 32 ›› Issue (3): 712.

• Articles • Previous Articles     Next Articles

Highly Diastereroselective Synthesis of Dihydrofurans Catalyzed by PE-supported Pyridinium

CHEN Shuai-Shuai1, LUO Shi-Zhong1, LI Jun-Fang2, LIU Chun-Rong2, SUN Xiu-Li2, TANG Yong2*   

  1. 1. Anhui Key Laboratory of Functional Molecular Solids, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China;
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
  • Received:2010-10-18 Revised:2011-01-09 Online:2011-03-10 Published:2011-02-23
  • Contact: Yong TANG E-mail:tangy@mail.sioc.ac.cn
  • Supported by:

    国家自然科学基金(批准号: 20904049)资助.

Abstract: The ylide reaction is one of the most useful approaches in forming ring compounds, and highly efficient catalysis of ylide reaction becomes one of the important frontiers in organic synthetic research. Polymer supported catalysis with tunable loading may increase the efficiency of the catalysis and avoid the volatilization of the ylide catalysis which might be savory and poisonous. In the presence of catalytic (O-NX) TiCl3 and MMAO, 4-(undec-10-enyl)pyridine was triumphantly inserted into the polyethylene chains. This PE supported pyridine proved to be an excellent recoverable and reusable organocatalyst. In the presence of catalytic amount of PE-supported pyridine and Fe(Tcpp)Cl, α-ylidene-β-diketones reacted with diazoacetate affording dihydrofurans respectively in up to 96% yield with high diastereoselectivities. The catalyst could be easily recovered after the reaction by cooling the reaction mixture to room temperature because the solubility of the PE-supported catalyst is dependent on the temperature and comonomer content. The yield of the reaction was almost maintained with excellent selectivity which was higher than 90% in 3 runs. This application allowed PE to be used as a cheap, readily prepared, easy separation, no-volatility, low noxious and recoverable catalyst support.

Key words: Non- Metallocene catalysts, Supported catalysts, Ylide, Dihydrofuran cyclization reaction

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