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.