Chiral phosphine Lewis base catalyzed asymmetric aza-Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone and phenyl acrylate

In the aza-Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone (MVK) promoted by chiral phosphine Lewis base: (R)-2ʹdiphenylphosphanyl-[1,1ʹ]binaphthalenyl-2-ol (10 mol%), the aza-Baylis–Hillman adducts 1 were obtained in good yields with high ee (70–94% ee) at –30 °C in THF. In CH2Cl2 upon heating at 40 °C, the aza-Baylis–Hillman reaction of N-sulfonated imines with phenyl acrylate gave the adducts 2 in high yields (60–97%) with moderate ee (52–77%).