{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T16:01:40Z","timestamp":1790784100951,"version":"4.1.0"},"reference-count":83,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T00:00:00Z","timestamp":1738713600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T00:00:00Z","timestamp":1738713600000},"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":["92156007, 22471143"],"award-info":[{"award-number":["92156007, 22471143"]}],"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":[[2025,2,24]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Planar chirality found tremendous use in many fields, such as chemistry, optics, and materials science. In particular, planar chiral [2.2]paracyclophanes (PCPs) are a type of structurally interesting and practically useful chiral compounds bearing unique electronic and photophysical properties and thus have been widely used in \u03c0\u2010stacking polymers, organic luminescent materials, and as a valuable toolbox for developing chiral ligands or organocatalysts. However, the synthesis of chiral PCP derivatives remains a longstanding challenge. Current synthetic methods primarily rely on chiral preparative liquid chromatography separation or chemical and kinetic resolution reactions. Here, we report an enantioconvergent alkynylation of an\n                    <jats:italic>in situ<\/jats:italic>\n                    \u2010formed dehydro\u2010[2,2]\u2010paracyclophane intermediate by asymmetric copper(I) catalysis. This approach enables the efficient synthesis of valuable planar chiral PCP building blocks and heterocycles with good yields and excellent enantioselectivity. The success of this reaction lies in the development of a practical route to access strained dehydro\u2010[2,2]\u2010paracyclophane intermediates, which can also be utilized in various strain\u2010release nucleophilic or cycloaddition reactions to synthesize diverse functionalized PCPs. DFT calculations of this reaction suggest that the enantioselectivity is determined by the aryne complexation with chiral copper(I) acetylide and the subsequent insertion reaction.\n                  <\/jats:p>","DOI":"10.1002\/anie.202420667","type":"journal-article","created":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T12:45:17Z","timestamp":1736772317000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Strained Dehydro\u2010[2,2]\u2010paracyclophane Enabled Planar Chirality Construction and [2.2]Paracyclophane Functionalization"],"prefix":"10.1002","volume":"64","author":[{"given":"Xue","family":"Zhang","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering Shandong University  Jinan 250100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi","family":"Zhou","sequence":"additional","affiliation":[{"name":"College of Chemistry Peking University  Beijing 100871 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhi\u2010Xiang","family":"Yu","sequence":"additional","affiliation":[{"name":"College of Chemistry Peking University  Beijing 100871 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chen\u2010Ho","family":"Tung","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Shandong University  Jinan 250100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3189-0777","authenticated-orcid":false,"given":"Zhenghu","family":"Xu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Shandong University  Jinan 250100 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"}]}],"member":"311","published-online":{"date-parts":[[2025,2,5]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.abm9596"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-38405-9"},{"key":"e_1_2_7_4_1","unstructured":"For selected reviews:"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2590"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm200584g"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00500"},{"key":"e_1_2_7_8_1","unstructured":"\u00a0"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2TC04885J"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-19479-1"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202217045"},{"key":"e_1_2_7_12_2","author":"Gong M.","year":"2024","journal-title":"Adv. Funct. Mater."},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC00694E"},{"key":"e_1_2_7_14_1","unstructured":"\u00a0"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600752"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aar8449"},{"key":"e_1_2_7_17_1","unstructured":"\u00a0"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205516"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202204926"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c01163"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00088a047"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c01046"},{"key":"e_1_2_7_23_1","unstructured":"\u00a0"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaz7381"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315603"},{"key":"e_1_2_7_26_2","author":"Li J.","year":"2024","journal-title":"Nat. Commun."},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-45218-x"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202316739"},{"key":"e_1_2_7_29_2","author":"Yang G.","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_30_1","unstructured":"\u00a0"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2020.05.003"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01176-3"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar50042a003"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00803A"},{"key":"e_1_2_7_35_1","unstructured":"\u00a0"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1038\/164915b0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202113504"},{"key":"e_1_2_7_38_1","unstructured":"\u00a0"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo962142a"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(98)00015-9"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(20022)2002:3<468::AID-EJOC468>3.0.CO;2-3"},{"key":"e_1_2_7_42_2","first-page":"4177","volume":"24","author":"Parmar R.","year":"2010","journal-title":"Synthesis"},{"key":"e_1_2_7_43_1","unstructured":"\u00a0"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(01)00452-9"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200500386"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201501153"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9QO01011D"},{"key":"e_1_2_7_48_2","author":"Liu Q.","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-40718-8"},{"key":"e_1_2_7_50_1","unstructured":"\u00a0"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b01872"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-47407-0"},{"key":"e_1_2_7_53_1","unstructured":"\u00a0"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c01292"},{"key":"e_1_2_7_55_2","author":"Chen D.","year":"2024","journal-title":"CCS Chem."},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01109a523"},{"key":"e_1_2_7_57_1","unstructured":"\u00a0"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19560890539"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature17429"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c10225"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00608"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01011"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00262"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5099935"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390151"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107485"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00350E"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00825"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.ade0032"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1039\/b901970g"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/c29690001358"},{"key":"e_1_2_7_72_1","unstructured":"\u00a0"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1983.1211"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0358612"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo500819w"},{"key":"e_1_2_7_76_1","unstructured":"Deposition numbers 2380667 (for10) 2380679 (for11) 2385577 (for12\u2032) 2385578 (for13\u2032) 2380683 (for30) and 2383045 (for48) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_7_77_1","unstructured":"\u00a0"},{"key":"e_1_2_7_78_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-020-2701-2"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202006016"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c09594"},{"key":"e_1_2_7_81_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800969"},{"key":"e_1_2_7_82_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904863"},{"key":"e_1_2_7_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100785a001"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202420667","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202420667","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202420667","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T15:05:40Z","timestamp":1790780740000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202420667"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,2,5]]},"references-count":83,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2025,2,24]]}},"alternative-id":["10.1002\/anie.202420667"],"URL":"https:\/\/doi.org\/10.1002\/anie.202420667","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,2,5]]},"assertion":[{"value":"2024-10-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-02-05","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202420667"}}