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Transition Metal-Catalyzed Regioselective and Stereoselective Aminochlorination of Cinnamic Esters

Guigen Li, Han-Xun Wei, Sun Hee Kim and Margret Neighbors

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

G. Li, H.-X. Wei, S. H. Kim, M. Neighbors, Org. Lett., 1999, 1, 395-397.

DOI: 10.1021/ol990059e


An aminohalogenation of cinnamic esters with N,N-dichloro-p-toluenesulfonamide provides vicinal chloroamine derivatives in very good yields. The reaction was performed in MeCN using ZnCl2 or Cu(OTf)2 as catalyst. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.

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Key Words

sulfonamides, 1,2-chloroamines

ID: J54-Y1999