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Regio- and Stereoselective Copper-Catalyzed Synthesis of Vicinal Haloamino Ketones from α,β-Unsaturated Ketones

Dianjun Chen, Cody Timmons, Steven Chao, Guigen Li*

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA, Email:

D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004, 3097-3101.

DOI: 10.1002/ejoc.200400050


The regio- and stereoselective aminochlorination of α,β-unsaturated ketones with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) and CuOTf as catalyst provides an easy access to vicinal haloamino ketones, with excellent regioselectivity and good yields. Aromatic and aliphatic enones give opposite regioselectivity.

see article for more examples

Copper-Catalyzed Aminohalogenation Using the 2-NsNCl2/2-NsNHNa Combination as the Nitrogen and Halogen Sources for the Synthesis of anti-Alkyl 3-Chloro-2-(o-nitrobenzenesulfonamido)-3-arylpropionates

G. Li, H.-X. Wei, S. H. Kim, Org. Lett., 2000, 2, 2249-2252.

Key Words

Aminochlorination, α,β-Unsaturated Ketones, Haloamines, β-Amino ketones, α-Amino ketones, α-Chloro ketones, Benzylchlorides

ID: J24-Y2004-560