Regio- and stereoselective synthesis of anti-1,3-diaryl-3-chloro-2-(o- nitrophenylsulfonylamino)-3-propan-1-ones through catalytic aminohalogenation reaction of α,β-unsaturated ketones

The synthesis of anti-1,3-diaryl-3-chloro-2-(2-nitrophenylsulfonylamino)-3- propan-1-ones has been achieved. The aminohalogenation of α,β- unsaturated ketones resulted in the vicinal haloamine products in high regio- and stereoselectivity and modest to good chemical yields. The reaction can be conducted under convenient conditions by using the combination of 2-NsNCl ₂/2-NsNHNa (2-Ns = 2-nosyl = 2-nitrophenylsulfonyl) as the nitrogen/chlorine source and by using copper(I) triflate as the catalyst. An N-(2-nosyl)-N-H-aziridinium intermediate was proposed to exist in the aminohalogenation process.