Copper-Catalyzed Aminohalogenation Using the 2-NsNCl₂/2-NsNHNa Combination as the Nitrogen and Halogen Sources for the Synthesis of <i>a</i><i>nti</i>-Alkyl 3-Chloro-2-(<i>o</i>-nitrobenzenesulfonamido)-3-arylpropionates

Abstract

New regio- and stereoselective aminohalogenation of cinnamic esters has been developed using the combination of 2-NsNCl(2)/2-NsNHNa as the nitrogen and chlorine sources and copper(I) triflate as the catalyst. The new procedure provides an efficient synthesis of anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-phenylpropionate derivatives. Nine examples are presented with good yields (62-82%) and stereoselectivity ((5:1)-(30:1)).