Octa-1,7-diene-4,5-diamine Derivatives: Useful Intermediates for the Stereoselective Synthesis of Nitrogen Heterocycles and Ligands for Asymmetric Catalysis

The octa-1,7-diene-4,5-diamine skeleton is usually prepared by the addition of allylic organometallic reagents to glyoxal diimines. The relative and absolute configurations of the C4 and C5 stereocenters are dependent on the nature of the (chiral) nitrogen substituents. These compounds are useful intermediates for the construction of NHC carbene complexes and nitrogen heterocycles, such as 2,2′-bipyrrolidines, 2,5-diazabicyclo[2.2.1]heptanes, amino- and hydroxy-substituted 7-azanorbornane, and diamino-substituted cyclohexanols and cyclohexanediols.