{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T10:19:02Z","timestamp":1790072342636,"version":"4.0.1"},"reference-count":95,"publisher":"Wiley","issue":"51","license":[{"start":{"date-parts":[[2024,10,30]],"date-time":"2024-10-30T00:00:00Z","timestamp":1730246400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2024,10,30]],"date-time":"2024-10-30T00:00:00Z","timestamp":1730246400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22301250"],"award-info":[{"award-number":["22301250"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2024,12,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The dehydro\u2010Diels\u2013Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper\u2010catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom\u2010economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non\u2010noble metal\u2010catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis.<\/jats:p>","DOI":"10.1002\/anie.202411709","type":"journal-article","created":{"date-parts":[[2024,9,13]],"date-time":"2024-09-13T03:47:31Z","timestamp":1726199251000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["Copper\u2010Catalyzed Enantioselective Dehydro\u2010Diels\u2013Alder Reaction: Atom\u2010Economical Synthesis of Axially Chiral Carbazoles"],"prefix":"10.1002","volume":"63","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  361005 Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang\u2010Bo","family":"Chen","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  361005 Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun\u2010Zhe","family":"Gao","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  361005 Xiamen 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  361005 Xiamen China"},{"name":"State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences  200032 Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5551-678X","authenticated-orcid":false,"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  361005 Xiamen China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,10,30]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00825"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503571"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00126"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/9781118629871"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0783986"},{"key":"e_1_2_7_7_1","unstructured":"For selected examples on the DDA reaction of dienes with alkynes see:"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00802"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-03534-z"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol501853y"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301938z"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202283d"},{"key":"e_1_2_7_13_1","unstructured":"For selected examples on the DDA reaction of enynes with alkenes or alkynes see:"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c02469"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207510"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04390G"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201807136"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01145"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201804529"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol5034332"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201302960"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300570"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.06.024"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja075794x"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050609a"},{"key":"e_1_2_7_26_1","unstructured":"For selected examples on the DDA reaction of diynes with alkenes or alkynes see:"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c00877"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC00960D"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0075-y"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b03832"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature17429"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405903"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature11518"},{"key":"e_1_2_7_34_1","unstructured":"For selected examples on hetero-DDA reaction see:"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11243"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja7112917"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810174"},{"key":"e_1_2_7_38_1","unstructured":"For selected reviews on vinyl cations see:"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-021-1117-2"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810701"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0100374"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197803331"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.ade5320"},{"key":"e_1_2_7_44_1","unstructured":"For recent reviews on ynamide reactivity see:"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00743"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00283F"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00769B"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00474J"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00417"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c04180"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b01851"},{"key":"e_1_2_7_52_2","first-page":"59","volume":"48","author":"Evano G.","year":"2015","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar400193g"},{"key":"e_1_2_7_54_1","unstructured":"For selected examples on chiral copper-catalyzed 1 5-diyne cyclization see:"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-46288-7"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-42805-2"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303670"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC06152J"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202210637"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202115554"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC02773E"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c01918"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b09303"},{"key":"e_1_2_7_64_1","unstructured":"For selected reviews on the application of axial chirality see:"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00500"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00121D"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400568b"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100155e"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527635207"},{"key":"e_1_2_7_70_1","unstructured":"For selected reviews on the construction of axial chirality see:"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-024-00618-x"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-024-01138-z"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303966"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00175"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00486"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00465"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00417"},{"key":"e_1_2_7_78_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO01699G"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00870B"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01306"},{"key":"e_1_2_7_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c03459"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC03967H"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00136"},{"key":"e_1_2_7_84_1","unstructured":"For more details see the Supporting Information."},{"key":"e_1_2_7_85_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar800104y"},{"key":"e_1_2_7_86_1","unstructured":"Deposition numbers CCDC 2350040 (2\u2009c) and CCDC 2356796 (rac-4\u2009b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_7_87_1","unstructured":"For selected examples on noble-metal catalyzed enantioselective 1 6-diyne cyclization see:"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202202542"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300696"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060348f"},{"key":"e_1_2_7_91_1","unstructured":"For selected examples see:"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b00997"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/np300464t"},{"key":"e_1_2_7_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja003488c"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00377a014"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202411709","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202411709","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202411709","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,5]],"date-time":"2026-09-05T16:56:32Z","timestamp":1788627392000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202411709"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,10,30]]},"references-count":95,"journal-issue":{"issue":"51","published-print":{"date-parts":[[2024,12,16]]}},"alternative-id":["10.1002\/anie.202411709"],"URL":"https:\/\/doi.org\/10.1002\/anie.202411709","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,10,30]]},"assertion":[{"value":"2024-06-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-10-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202411709"}}