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

Guigen Li, Han-Xun Wei and Sun Hee Kim

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, Email: guigen.littu.edu

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

DOI: 10.1021/ol000120b

Abstract

The combination of 2-NsNCl2/2-NsNHNa as the nitrogen and chlorine sources and copper(I) triflate as the catalyst enables a regio- and stereoselective aminochlorination of cinnamic esters to provide anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-phenylpropionate derivatives with good yields and stereoselectivity.

see article for more examples

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

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

Key Words

1,2-chloroamines, benzyl chlorides

ID: J54-Y2000

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

Guigen Li, Han-Xun Wei and Sun Hee Kim

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