Axially Chiral Guanidine as Highly Active and Enantioselective Catalyst for Electrophilic Amination of Unsymmetrically Substituted 1,3-Dicarbonyl Compounds

A newly designed axially chiral guanidine is found to function as an effective platform for asymmetric induction at the alpha-carbon of unsymmetrically substituted 1,3-dicarbonyl compounds. Highly efficient and enantioselective electrophilic amination of various 1,3-dicarbonyl compounds with azodicarboxylate was successfully achieved using the present chiral guanidine catalyst, which provides efficient access to the construction of nitrogen-substituted quaternary stereocenters in an optically active form.