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Isodesmic reactions provide a complementary skeletal editing approach for the redistribution of chemical bonds in chemical synthesis. However, catalytic enantioselective isodesmic reaction is extremely scarce and enantioselective isodesmic reaction to synthesize atropisomeric compounds is unknown. Herein, we report a facile method to synthesize axially chiral aminoaryl quinoxalines through Cu(I)\u2010catalyzed dearomatization and sequential chiral phosphoric acid (CPA) catalyzed enantioselective isodesmic C\u2212N bond formation and cleavage from indoles and 1,2\u2010diaminoarenes under mild reaction conditions. In this process, the five\u2010membered ring of the indole scaffold was broken and a novel quinoxaline skeleton was constructed. This method allows the practical and atom\u2010economical synthesis of valuable axially chiral aminoaryl quinoxalines in high yields (up to 95\u2009%) and generally excellent enantioselectivities (up to 99\u2009% ee). Notably, this novel type of quinoxaline atropisomers has promising applications in developing axially chiral ligand in asymmetric catalysis. This strategy represents the first example of CPA\u2010catalyzed enantioselective isodesmic reaction to form axially chiral compounds.<\/jats:p>","DOI":"10.1002\/anie.202420390","type":"journal-article","created":{"date-parts":[[2024,12,17]],"date-time":"2024-12-17T03:35:35Z","timestamp":1734406535000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Copper\u2010Catalyzed Enantioselective Skeletal Editing through a Formal Nitrogen Insertion into Indoles to Synthesize Atropisomeric Aminoaryl Quinoxalines"],"prefix":"10.1002","volume":"64","author":[{"given":"Xu","family":"Zhang","sequence":"first","affiliation":[{"name":"State key laboratory for Chemistry and Molecular Engineering of Medicinal Resources Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) Collaborative Innovation Center for Guangxi Ethnic Medicine School of Chemistry and Pharmaceutical 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