Synthesis of Amino-Functionalized Sulfonimidamides and Their Application in the Enantioselective Henry Reaction

Amino-functionalized sulfonimidamides have been prepared by aziridinium ring-opening reactions and nucleophilic substitutions of sulfonimidoyl chlorides. Whereas the former reactions afford separable diastereomeric products, the latter provide single stereoisomers. Application of the resulting stereochemically homogeneous sulfonimidamides as ligands in asymmetric copper-catalyzed Henry reactions of aromatic aldehydes with nitromethane led to products with enantioselectivities up to 95% ee in good yields.