Aminative Umpolung Synthesis of Aryl Vicinal Diamines from Aromatic Aldehydes

In this paper an aminative umpolung synthesis of aryl vicinal diamines from aldehydes and <i>N</i>-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 <i>N</i>-Ts imines to give a variety of 1,2-diamine derivatives in good yields with high <i>syn</i>/<i>anti</i> diastereoselectivity