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Owing to their unique architectures, calix[4]arenes have shown considerable potential in molecular recognition, catalysis, sensing, nanotechnology, and biotechnology. Herein, we report the first palladium‐catalyzed enantioselective C(sp 2 )–H cycloimidoylation for the versatile synthesis of inherently chiral calix[4]arenes incorporating a phenanthridine moiety. Notably, the double C(sp 2 )–H imidoylative annulation of calix[4]arene‐derived bisisocyanides affords unique inherently chiral calix[4]arenes embedded with bis‐phenanthridine units. More details are discussed in the article by Luo et al . on pages 771—776. image