Aminative Umpolung Synthesis of Aryl Vicinal Diamines from Aromatic Aldehydes

In this paper an aminative umpolung synthesis of aryl vicinal diamines from aldehydes and N-Ts imines is described. Electrophilic aromatic aldehydes were smoothly converted into delocalized 2-azaallylanions via condensation with 2,2-diphenylglycine in methanol and subsequent decarboxylation in THF and underwent further reaction with N-Ts imines to give a variety of 1,2-diamine derivatives in good yields with high syn/anti diastereoselectivity.