Stabilization of radicals by imides. A modular stereoselective approach to protected functional 1,2-diamines.

Songzhe Han (1) , Samir Z Zard (1)

1 DCSO - Laboratoire de synthèse organique

Radical addition of various xanthates to N,N'-diacylimidazol-2-one occurs readily to give protected 1,2-diamines. The imide group stabilizes the adduct radical sufficiently to enable a second addition to unactivated alkenes. In some cases, the addition product could be converted into an indoline, a tetralone, or further added to an indole. Regioselective removal of one acyl group could also be accomplished.

Domaines: Chimie organique

Songzhe Han, Samir Z Zard. Stabilization of radicals by imides. A modular stereoselective approach to protected functional 1,2-diamines.. Letters in Organic Chemistry, 2014, 16 (20), pp.5386-5389. ⟨hal-01098821⟩