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

Wen Dai; Yuan Mi; Ying Lv; Sensen Shang; Guosong Li; Guangwen Chen; Shuang Gao

doi:10.1055/s-0035-1561955

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(16): 2653-2658
DOI: 10.1055/s-0035-1561955

special topic

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

Wen Dai

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

,

Yuan Mi

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

,

Ying Lv

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

,

Sensen Shang

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

,

Guosong Li

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

,

Guangwen Chen*

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

,

Shuang Gao*

Dalian Institute of Chemical Physics, The Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. of China eMail: gwchen@dicp.ac.cn eMail: sgao@dicp.ac.cn

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Abstract

Alle Artikel dieser Rubrik

‡ These authors contributed equally to this work.

Abstract

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.

Key words

continuous flow - microreactor - asymmetric epoxidation - iron catalysis - electron-deficient olefins - biomimetic catalyst

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