Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Propargylic Amines

An efficient kinetic resolution of primary propargylic amines with s-factors of up to 56 is reported. The strategy is based on a dual catalytic approach, namely the use of a newly developed and easy-to-make thiourea-amide anion binding catalyst in combination with 4-(dimethylamino)pyridine (DMAP), both employed at a 5 mol% catalyst loading. Benzylic amines are also resolved with s-factors of up to 38.