The synthesis of chiral N-tosylatedaminoimine ligands and their application in enantioselective addition of phenylacetylene to imines

A class of new chiral tridentate N-tosylatedaminoimine ligands were synthesized and used in the Cu(I)-catalyzed enantioselective addition of phenylacetylene to imines. Good enantioselectivities in up to 91% ee were obtained.

New chiral tridentate N-tosylatedaminoimine ligands were synthesized and were used in the Cu(I)-catalyzed enantioselective addition of alkynes to imines. Good enantioselectivities (up to 91% ee) were obtained.Figure optionsDownload as PowerPoint slide

N-((1R,2R)-2-((E)-2-Hydroxybenzylideneamino)-1,2-diphenylethyl)-4-methylbenzenesulfonamideC28H26N2O3S[α]D25=+12.1 (c 3.0, CH2Cl2)Source of chirality: (R,R)-1,2-diphenylethane-1,2-diamineAbsolute configuration: (R,R)

N-((1R,2R)-2-((E)-3,5-Di-tert-butyl-2-hydroxybenzylideneamino)-1,2-diphenylethyl)-4-methylbenzenesulfonamideC36H42N2O3S[α]D25=+17.9 (c 3.0, CH2Cl2)Source of chirality: (R,R)-1,2-Diphenylethane-1,2-diamineAbsolute configuration: (R,R)