Copper-catalyzed aminohalogenation using the 2-NsNCl(2)/2-NsNHNa combination as the nitrogen and halogen sources for the synthesis of anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-arylpropionates.
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)).
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. qeggl@ttu.edu
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D000586:Amination; D000588:Amines / Q000378:metabolism; D002384:Catalysis; D002713:Chlorine / Q000378:metabolism*; D002934:Cinnamates / Q000737:chemistry / Q000378:metabolism*; D003300:Copper / Q000378:metabolism*; D009584:Nitrogen / Q000378:metabolism*; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D000588:Amines; D002934:Cinnamates; D011422:Propionates; D013449:Sulfonamides; D002713:Chlorine; D003300:Copper; D009584:Nitrogen