Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 11557-11570Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01124
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Funding
- Fundamental Research Funds for the Central Universities [YJ201805, YJ201864]
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A unified strategy based on a key catalytic syn-selective Henry reaction was reported for the efficient synthesis of four antibiotics. The synthesis involved exploring the stereochemistry of copper(II)-catalyzed aryl aldehyde Henry reactions to create a challenging structure unit with vicinal stereocenters, followed by multistep continuous flow manipulations for efficient asymmetric synthesis of the antibiotics.
A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.
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