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

页码：2653 / 2658

页数：6

共 50 条

[21] Organocatalyzed styrene epoxidation accelerated by continuous-flow reactor
Yuan, Wei-Qiang
Zhou, Shou-Quan
Jiang, Yu-Yan
Li, Hao-Hong
Zheng, Hui-Dong
JOURNAL OF FLOW CHEMISTRY, 2020, 10 (01) : 227 - 234
[22] Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines
Chen, Xiangning
Gao, Bao
Su, Yijin
Huang, Hanmin
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) : 2535 - 2541
[23] Synthesis of Defined Poly(silsesquioxane)s: Fast Polycondensation of Trialkoxysilanes in a Continuous-Flow Microreactor
Kessler, Daniel
Loewe, Holger
Theato, Patrick
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2009, 210 (10) : 807 - 813
[24] Substitution effects on the catalytic activity of Mn(III)-porphyrins in epoxidation of alkenes with iodosylbenzene: A comparison between the electron-rich and electron-deficient porphyrins
Zakavi, Saeed
Ebrahimi, Leila
POLYHEDRON, 2011, 30 (10) : 1732 - 1738
[25] Electrochemical fluoro-selenenylation of electron-deficient olefins
Nagura, Hirokatsu
Inagi, Shinsuke
Fuchigami, Toshio
TETRAHEDRON, 2009, 65 (08) : 1559 - 1566
[26] Photosensitized addition of isopropanol to furanones in a continuous-flow dual capillary microreactor
Yavorskyy, Alexander
Shvydkiv, Oksana
Nolan, Kieran
Hoffmann, Norbert
Oelgemoeller, Michael
TETRAHEDRON LETTERS, 2011, 52 (02) : 278 - 280
[27] Continuous-flow diazotization of methyl anthranilate in microreactor system
Wang B.
Wang C.
Yin J.
Huagong Jinzhan/Chemical Industry and Engineering Progress, 2021, 40 (10): : 5678 - 5691
[28] Experimental investigation of mononitrotoluene preparation in a continuous-flow microreactor
Anming Yang
Jincai Yue
Shiqing Zheng
Xia Yang
Lingqi Kong
Dongjian Zhou
Litao Qin
Hua Zhong
Research on Chemical Intermediates, 2022, 48 : 4373 - 4390
[29] 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
[30] Ultrafast synthesis of isoquercitrin by enzymatic hydrolysis of rutin in a continuous-flow microreactor
Wang, Jun
Gong, An
Gu, Shuangshuang
Cui, Hongsheng
Wu, Xiangyang
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2015, 80 (07) : 853 - 866

← 1 2 3 4 5 →