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Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

Yingqi Xia, Meifen Jiang, Minjie Liu, Yan Zhang, Hongmin Qu, Tong Xiong, Huashan Huang, Dang Cheng and Fener Chen*

*Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China, Email:

Y. Xia, M. Jiang, M. Liu, Y. Zhang, H. Qu, T. Xiong, H. Huang, D. Cheng, F. Chen, J. Org. Chem., 2021, 86, 11557-11570.

DOI: 10.1021/acs.joc.1c01124

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A ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol provides challenging syn-2-amino-1,3-diols with vicinal stereocenters with excellent stereocontrol. Subsequent multistep continuous flow manipulations achieve an efficient asymmetric synthesis of a family of amphenicol antibiotics.

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Key Words

Henry Reaction

ID: J42-Y2021