Enantioselective and Enantioconvergent Iron-Catalyzed C(sp3)-H Aminations to Chiral 2-Imidazolidinones

Abstract

Enantioselective or enantioconvergent iron-catalyzed ring-closing C(sp3)-H aminations of N-aroyloxyurea through intermediate iron nitrene species provide chiral 2-imidazolidinones in up to 99% yield and with up to 95% ee (40 examples). This is a rare example in which sustainable iron catalysis is combined with C(sp3)-H amination and asymmetric catalysis. Chiral 2-imidazolidinones are prevalent structural motifs in bioactive molecules and can also be hydrolyzed to valuable chiral vicinal diamines in a single step. (Figure presented.).