Development of a Continuous-Flow Microreactor for Asymmetric Epoxidation of Electron-Deficient Olefins

被引：11
|
作者：
Dai, Wen
Mi, Yuan
Lv, Ying
Shang, Sensen
Li, Guosong
Chen, Guangwen [1 ]
Gao, Shuang [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 16期
基金：
中国博士后科学基金;
关键词：
continuous flow; microreactor; asymmetric epoxidation; iron catalysis; electron-deficient olefins; biomimetic catalyst; HIGHLY STEREOSELECTIVE EPOXIDATION; ENANTIOSELECTIVE EPOXIDATION; HYDROGEN-PEROXIDE; ALPHA; BETA-UNSATURATED KETONES; CATALYSIS; ALKENES; OXIDATION; ORGANOCATALYSIS; COMPLEXES; SYSTEM;
D O I：
10.1055/s-0035-1561955
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric epoxidation of electron-deficient olefins catalyzed by a biomimetic iron complex in a continuous-flow microreactor is described. The reaction conducted in the microreactor is characterized by rapid (<4 min) epoxidation of trisubstituted enones in high yields (up to 90%) and excellent enantioselectivities (up to 92% ee); compared to its batchwise counterpart, the microreactor reaction also allows shorter reaction times, safer operation, and more precise control over the reaction conditions.
引用
收藏
页码：2653 / 2658
页数：6
相关论文
共 50 条
  • [41] Experimental investigation of mononitrotoluene preparation in a continuous-flow microreactor
    Yang, Anming
    Yue, Jincai
    Zheng, Shiqing
    Yang, Xia
    Kong, Lingqi
    Zhou, Dongjian
    Qin, Litao
    Zhong, Hua
    RESEARCH ON CHEMICAL INTERMEDIATES, 2022, 48 (10) : 4373 - 4390
  • [42] Epoxidation of electron-deficient alkenes using heterogeneous basic catalysts
    Fraile, I.M.
    García, J.I.
    Marco, D.
    Mayoral, J.A.
    Sánchez, E.
    Monzón, A.
    Romeo, E.
    1673, Elsevier Inc. (130 B)
  • [43] Continuous-flow synthesis of azo dyes in a microreactor system
    Wang, Fajun
    Huang, Jinpei
    Xu, Jianhong
    CHEMICAL ENGINEERING AND PROCESSING-PROCESS INTENSIFICATION, 2018, 127 : 43 - 49
  • [44] PALLADIUM-ASSISTED FUNCTIONALIZATION OF OLEFINS - A NEW AMINATION OF ELECTRON-DEFICIENT OLEFINS
    BOZELL, JJ
    HEGEDUS, LS
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12): : 2561 - 2563
  • [45] Epoxidation of chiral electron-deficient alkenes with basic heterogeneous catalysts
    Fraile, JM
    García, JI
    Marco, D
    Mayoral, JA
    APPLIED CATALYSIS A-GENERAL, 2001, 207 (1-2) : 239 - 246
  • [46] Rhodium-catalyzed asymmetric addition of organo-boron and -titanium reagents to electron-deficient olefins
    Hayashi, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (01) : 13 - 21
  • [47] Copper hydride-catalyzed reduction of electron-deficient olefins
    Ai-Jun Zheng
    Feng-Jun Shan
    Zheng-Ning Li
    Zeng-Chang Li
    Lan Jiang
    Chemical Papers, 2013, 67 : 1271 - 1276
  • [48] Epoxidation of electron-deficient olefins by a nucleophilic iron(III) peroxo porphyrinato complex, peroxo(tetramesitylporphyrinato)ferrate(1-)
    Sisemore, MF
    Burstyn, JN
    Valentine, JS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02): : 206 - 208
  • [49] Highly Enantioselective Bioinspired Epoxidation of Electron-Deficient Olefins with H2O2 on Aminopyridine Mn Catalysts
    Ottenbacher, Roman V.
    Samsonenko, Denis G.
    Talsi, Evgenii P.
    Bryliakov, Konstantin P.
    ACS CATALYSIS, 2014, 4 (05): : 1599 - 1606
  • [50] Catalytic Enantioselective Reductive Cross Coupling of Electron-Deficient Olefins
    Cao, Kangning
    Li, Chunyang
    Tian, Dong
    Zhao, Xiaowei
    Yin, Yanli
    Jiang, Zhiyong
    ORGANIC LETTERS, 2022, : 4788 - 4792
12345