Asymmetric Peroxidation of Imines

Peroxide-containing compounds are found in natural products such as artemisinin (qinghaosu), the antimalarial, with chiral amino peroxides in compounds such as verruculogen (1,) which alters GABA receptor binding and dioxetanone, which gives rise to the light emittance in the Japanese firefly.  A recent paper describes a simple method of asymmetrically peroxidising imines to give alpha amino peroxides (Zheng W et al, Angew Chem Int Ed, 2010, 49, 6591.).  The peroxidation occurs with t-butylhydroperoxide in the presence of chiral phosphoric acids based on binaphthol at RT. Best results were in IPAc as solvent. Toluene and THF giving lower ee.