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However, the catalytic enantioselective coupling of carboxylic acids remains elusive, especially for the atroposelective reaction. Here we report a chiral Br\u00f8nsted acid (CBA)\u2010catalyzed atroposelective coupling of carboxylic acids with amines and alcohols using ynamides as coupling reagents. The novel enantiocontrol involving CBA\u2010catalyzed ester addition enables the straightforward construction of axially chiral amides and planar\u2010chiral esters with high enantioselectivities through atroposelective intermolecular amidation and intramolecular macrolactonization. Diverse medicinally relevant carboxylic acids can undergo direct late\u2010stage modification by this method. Importantly, this reaction represents the first atroposelective coupling of carboxylic acids with amines, as well as the first chemocatalytic atroposelective coupling of carboxylic acids with alcohols. The resulting atropisomeric skeletons can be readily derivatized to chiral ligands and catalysts for asymmetric catalysis.<\/jats:p>","DOI":"10.1002\/anie.202505167","type":"journal-article","created":{"date-parts":[[2025,3,20]],"date-time":"2025-03-20T04:04:15Z","timestamp":1742443455000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":34,"title":["Br\u00f8nsted Acid\u2010Catalyzed Atroposelective Coupling of Carboxylic Acids with Amines and Alcohols via Ynamide Mediation"],"prefix":"10.1002","volume":"64","author":[{"given":"Hua\u2010Hong","family":"Chen","sequence":"first","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia\u2010Tian","family":"Jiang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ye\u2010Nan","family":"Yang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Long\u2010Wu","family":"Ye","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 China"},{"name":"State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences  Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo","family":"Zhou","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,3,27]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/0470084960"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-018-0211-5"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature10702"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00237"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60345H"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/B923093A"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100048w"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0301402"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-024-00591-9"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101028"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja103490h"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/c001075h"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705643"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2003.10.210"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)80817-5"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaz7381"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00743"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00283F"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00474J"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00769B"},{"key":"e_1_2_7_21_1","first-page":"59","volume":"48","author":"Evano G.","year":"2015","journal-title":"Aldrichim. 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