Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide

被引:0
|
作者
Zhao Pan [1 ]
Lu Cui-fen [1 ]
Yang Gui-chun [1 ]
Chen Zu-xing [1 ]
Dong Nian-guo [2 ]
Shi Jia-wei [2 ]
机构
[1] Hubei Univ, Key Lab Synth & Applicat Organ Funct Mol, Minist Educ, Coll Chem & Chem Engn, Wuhan 430000, Peoples R China
[2] Huazhong Sci & Technol Univ, Dept Cardiovarscular Surg, Union Hosp, Tongji Med Coll, Wuhan 430072, Peoples R China
基金
国家高技术研究发展计划(863计划);
关键词
Poly(ethylene glycol); Pyridinium ylide; Synthesis; Cyclopropane; TRANSFER-CATALYZED CONDITIONS; SOLUBLE SUPPORT; ORGANIC-SYNTHESIS; ASYMMETRIC CYCLOPROPANATION; DERIVATIVES; CIS-1-ARYL-2-BENZOYL-3,3-DICYANOCYCLOPROPANES; ELIMINATION; CYCLIZATION; LIBRARY; WATER;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polysubstituted cyclopropanes were efficiently prepared with poly(ethylene glycol)(PEG) as soluble support. The reaction of PEG-supported pyridinium ylide with arylidenemalononitrilc(R=CN) or ethyl arylidenecyanoacetate(R=COOEt) in the presence of triethylamine(TEA) afforded PEG-supported cyclopropanecarboxylates, which were cleaved by 1% KCN/EtOH to obtain polysubstituted cyclopropanes with exclusive trans-selectivity and good yields.
引用
收藏
页码:984 / 987
页数:4
相关论文
共 50 条
  • [1] Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide
    ZHAO Pan1
    2.Department of Cardiovarscular Surgery
    Chemical Research in Chinese Universities, 2011, 27 (06) : 984 - 987
  • [2] Pyridinium Ylide-Assisted One-Pot Two-Step Tandem Synthesis of Polysubstituted Cyclopropanes
    Wang, Qi-Fang
    Song, Xiao-Kai
    Chen, Jiao
    Yan, Chao-Guo
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (06): : 1007 - 1010
  • [3] Pyridinium ylide-assisted KY zeolite catalyzed tandem synthesis of polysubstituted cyclopropanes
    Rama, Velladurai
    Kanagaraj, Kuppusamy
    Subramanian, Thirumeni
    Suresh, Palaniswamy
    Pitchumani, Kasi
    CATALYSIS COMMUNICATIONS, 2012, 26 : 39 - 43
  • [4] Poly(ethylene glycol) supported synthesis of heterocyclic libraries
    Lin, XF
    Wang, YG
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (10) : 1157 - 1166
  • [5] Synthesis of poly(ethylene glycol) derivatives
    Chen, Hai-Yun
    Shan, Yu-Kai
    Qin, Yu-Yue
    Zhou, Guo-Xian
    Yuan, Ming-Long
    ADVANCED ENGINEERING MATERIALS III, PTS 1-3, 2013, 750-752 : 1674 - +
  • [6] Poly(ethylene glycol)-supported Piperazine-Synthesis and Application in Knoevenagel Condensation
    Wang Cui-e
    Jin Jie
    Zhang Min
    Yu Shu-yan
    Shang Yong-jia
    Hu Jin-song
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2010, 26 (02) : 263 - 267
  • [7] Synthesis of Branched Poly(ethylene glycol) by an Acetal Protection Method
    Li, Zhongyu
    Shan, Pengfei
    Li, Daai
    Zou, Xianglong
    POLYMER SCIENCE SERIES B, 2019, 61 (03) : 294 - 301
  • [8] Synthesis of carbon nanofibers from poly(ethylene glycol) with controlled structure
    Takahashi, Yusuke
    Fujita, Hirotaka
    Lin, Wan-Hua
    Li, Yuan-Yao
    Fujii, Takao
    Sakoda, Akiyoshi
    ADSORPTION-JOURNAL OF THE INTERNATIONAL ADSORPTION SOCIETY, 2010, 16 (1-2): : 57 - 68
  • [9] Synthesis of carbon nanofibers from poly(ethylene glycol) with controlled structure
    Yusuke Takahashi
    Hirotaka Fujita
    Wan-Hua Lin
    Yuan-Yao Li
    Takao Fujii
    Akiyoshi Sakoda
    Adsorption, 2010, 16 : 57 - 68
  • [10] Stereoselective synthesis of activated cyclopropanes with an α-pyridinium acetamide bearing an 8-phenylmenthyl group as the chiral auxiliary
    Kojima, S
    Hiroike, K
    Ohkata, K
    TETRAHEDRON LETTERS, 2004, 45 (18) : 3565 - 3568