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: guigen.littu.edu

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

DOI: 10.1002/ejoc.200400050

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Abstract

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.

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Key Words

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

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ID: J24-Y2004-560