Catalytic Asymmetric Peroxidation of Imines

Significance

Antilla and co-workers report the chiral phosphoric acid 1 catalyzed peroxidation of imines. In the presence of chiral 3,3′-bis-(9-­anthracenyl)-substituted BINOL phosphate 1, the addition of tert-butyl hydroperoxide to various aromatic imines proceeded smoothly to give the desired α-amino peroxides in generally high yields and enantioselectivities. The proposed transition state involves the dual activation of the imine and the hydroperoxide reagent via hydrogen bonding.