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However, catalytic enantioselective methods for de novo synthesis of such heterocycles remain scarce. Herein, a novel cyclizative rearrangement of readily available anilines and vicinal diketones for the one\u2010step construction of enantioenriched 2,2\u2010disubstituted indolin\u20103\u2010ones is presented. The reaction proceeds through a self\u2010sorted [3+2] heteroannulation\/regioselective dehydration\/1,2\u2010ester shift process. Only chiral phosphoric acid is employed to promote the entire sequence and simplify the manipulation of this protocol. Various common aniline derivatives are successfully applied to asymmetric synthesis as 1,3\u2010binuclephiles for the first time. Remarkably, the observed stereoselectivity is proposed to originate from an amine\u2010directed regio\u2010 and enantioselective <jats:italic>ortho<\/jats:italic>\u2010Csp<jats:sup>2<\/jats:sup>\u2010H addition of the anilines to the ketones. A range of synthetic transformations of the resulting products are demonstrated as well.<\/jats:p>","DOI":"10.1002\/advs.202402532","type":"journal-article","created":{"date-parts":[[2024,4,24]],"date-time":"2024-04-24T06:34:19Z","timestamp":1713940459000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2\u2010Disubstituted Indolin\u20103\u2010ones"],"prefix":"10.1002","volume":"11","author":[{"given":"Rui","family":"Quan","sequence":"first","affiliation":[{"name":"Shanghai Frontiers Science Center for Drug Target Identification and Delivery National Key Laboratory of Innovative Immunotherapy, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmaceutical Sciences Shanghai Jiao Tong University  800 Dongchuan Road, Minhang Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xing\u2010Zi","family":"Li","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center for Drug Target Identification and Delivery National Key Laboratory of Innovative Immunotherapy, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmaceutical Sciences Shanghai Jiao Tong University  800 Dongchuan Road, Minhang Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zi\u2010Qi","family":"Wang","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center for Drug Target Identification and Delivery National Key Laboratory of Innovative Immunotherapy, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmaceutical Sciences Shanghai Jiao Tong University  800 Dongchuan Road, Minhang Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu\u2010Ping","family":"He","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center for Drug Target Identification and Delivery National Key Laboratory of Innovative Immunotherapy, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmaceutical Sciences Shanghai Jiao Tong University  800 Dongchuan Road, Minhang Shanghai 200240 China"},{"name":"Department of Chemistry College of Sciences Shanghai University  Shanghai 200444 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0401-2434","authenticated-orcid":false,"given":"Hua","family":"Wu","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center for Drug Target Identification and Delivery National Key Laboratory of Innovative Immunotherapy, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmaceutical 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