Transition Metal-Catalyzed Regio- and Stereoselective Aminobromination of Olefins with TsNH2 and NBS as Nitrogen and Bromine Sources
Organic Letters2003Vol. 5(6), pp. 861–864
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Abstract
[reaction: see text] A new synthetic procedure for aminohalogenation of olefins has been developed for the preparation of vicinal haloamine derivatives in high yields by using Cu, Mn, or V catalysts with p-toluenesulfonamide (TsNH(2)) and N-bromosuccinimide (NBS) as nitrogen and bromine sources, respectively. Unprecedented regio- and stereoselectivity (anti:syn > 99:1) toward the aminohalogenation process is shown for olefinic substrates as well as transition metal catalysts.
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