Oxidative Kinetic Resolution of Alkyl-Substituted 1,2-Diamines

Chiral acyclic 1,2-diamines bearing alkyl-substituted stereocenters are privileged structural motifs in pharmaceuticals and agrochemicals. However, a catalytic asymmetric approach for these moieties has remained elusive. Here, we report a direct kinetic resolution of alkyl-substituted 1,2-diamines through titanium-catalyzed asymmetric oxidation to produce hydroxylamines. The practical method features a broad substrate scope, high levels of chiral recognition, good functional group tolerance, and high atom economy, enabling application in the synthesis of bioactive molecules that are difficult to obtain otherwise.