Diastereoselective Synthesis of 1,2-Diamines by Palladium Catalyzed Aza-Claisen Rearrangement

Abstract

In the thermal rearrangement of allylic trichloroacetimidates 6, no 1, 2-asymmetric induction can be observed. Palladium(II) catalyzed, however, the rearrangement takes place at 25°C and yields diastereoselectively (de ≥ 98%) the anti-1,2-diamines 7. The allylic trichloroacetimidates 6 can easily be prepared starting from α-amino acids.