Enantioselective Synthesis of Benzazepine Bearing a Diaryl Quaternary Carbon Center by Aryl Iodide-Catalyzed Asymmetric Desymmetrization

Chiral benzazepines are commonly found in a variety of bioactive molecules; however, efficient and modular approaches for constructing medium-sized rings remain challenging. Herein, we report an enantioselective synthesis of benzazepines bearing a diaryl quaternary carbon center via aryl iodide-catalyzed desymmetrization of 4,4-diarylpentanamides through asymmetric oxidative C-H amination, wherein chiral hypervalent iodine species serve as an alternative to transition-metal catalysts. The reaction features mild conditions, high yields, and excellent enantioselectivities (up to 97:3 er). Furthermore, the synthetic utility of this method has been demonstrated by scale-up synthesis and a series of synthetic transformations.