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Rapid Synthesis of α-Chiral Piperidines via a Highly Diastereoselective Continuous Flow Protocol

Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun* and Jinxing Ye*

*School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China, Email:,

C. Shan, J. Xu, L. Cao, C. Liang, R. Cheng, X. Yao, M. Sun, J. Ye, Org. Lett., 2022, 24, 3205-3240.

DOI: 10.1021/acs.orglett.2c00975


A practical continuous flow reaction of readily accessible N-(tert-butylsulfinyl)-bromoimine with Grignard reagents provides various enantioenriched α-substituted piperidines in good yields and high diastereoselectivities within minutes. The reaction can be scaled-up smoothly and an efficient synthesis of a drug precursor further showcases its utility.

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flow set-up

Key Words

piperidines, flow chemistry

ID: J54-Y2022