Synthesis 2016; 48(16): 2653-2658
DOI: 10.1055/s-0035-1561955
special topic
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 09 December 2015

Accepted after revision: 01 March 2016

Publication Date:
07 April 2016 (online)

‡ 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.

Supporting Information

 
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