Synthesis, characterization of ( R)-2,2′-diamino-1,1′-binaphthyl mono-sulfonamide and its ruthenium complex and evaluation of the catalytic properties in transfer hydrogenation reactions

Abstract

( R)-2-amino-2′-(8-quinolinesulfonyl amino)-1,1′-binaphthyl is synthesized. Its ruthenium complex is shown to be an asymmetric catalyst for transfer hydrogenation reactions in high chemical yield and modest enantioselectivity. Single crystal diffraction studies of both the ligand and the ruthenium complex show strong π-stacking interactions between the quinoline ring and one of the naphthyl groups. The relationship between the structure and catalytic reactivity is also discussed.