{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,13]],"date-time":"2026-09-13T19:01:49Z","timestamp":1789326109595,"version":"build-2803163510"},"reference-count":62,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2021,1,15]],"date-time":"2021-01-15T00:00:00Z","timestamp":1610668800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004663","name":"Ministry of Science and Technology, Taiwan","doi-asserted-by":"publisher","award":["109- 2634-F-007-023"],"award-info":[{"award-number":["109- 2634-F-007-023"]}],"id":[{"id":"10.13039\/501100004663","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004663","name":"Ministry of Science and Technology, Taiwan","doi-asserted-by":"publisher","award":["108-2622-8-007-017"],"award-info":[{"award-number":["108-2622-8-007-017"]}],"id":[{"id":"10.13039\/501100004663","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":[[2021,2,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This work reports gold\u2010catalyzed [3+2]\u2010annulations of \u03b1\u2010diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3\u2010dihydrofurans with high regio\u2010 and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]\u2010annulations with \u03b1\u2010diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.<\/jats:p>","DOI":"10.1002\/anie.202012611","type":"journal-article","created":{"date-parts":[[2020,11,24]],"date-time":"2020-11-24T06:30:32Z","timestamp":1606199432000},"page":"4479-4484","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Gold\u2010Catalyzed [3+2]\u2010Annulations of \u03b1\u2010Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity"],"prefix":"10.1002","volume":"60","author":[{"given":"Ching\u2010Nung","family":"Chen","sequence":"first","affiliation":[{"name":"Frontier Research Center for Matter Science and Technology and Department of Chemistry National Tsing-Hua University  Hsinchu Taiwan, ROC"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei\u2010Min","family":"Cheng","sequence":"additional","affiliation":[{"name":"Frontier Research Center for Matter Science and Technology and Department of Chemistry National Tsing-Hua University  Hsinchu Taiwan, ROC"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jian\u2010Kai","family":"Wang","sequence":"additional","affiliation":[{"name":"Frontier Research Center for Matter Science and Technology and Department of Chemistry National Tsing-Hua University  Hsinchu Taiwan, ROC"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tzu\u2010Hsuan","family":"Chao","sequence":"additional","affiliation":[{"name":"Department of Chemistry National Cheng Kung University  East District Tainan City Taiwan, ROC"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8121-0485","authenticated-orcid":false,"given":"Mu\u2010Jeng","family":"Cheng","sequence":"additional","affiliation":[{"name":"Department of Chemistry National Cheng Kung University  East District Tainan City Taiwan, ROC"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2011-8124","authenticated-orcid":false,"given":"Rai\u2010Shung","family":"Liu","sequence":"additional","affiliation":[{"name":"Frontier Research Center for Matter Science and Technology and Department of Chemistry National Tsing-Hua University  Hsinchu Taiwan, ROC"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,1,15]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For reviews for catalytic cyclopropanations 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These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_2_39_1","unstructured":"For gold-catalyzed asymmetric annulations of 1 3-dienes; see:"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901649s"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905415r"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902622b"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.9.264"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0sc00630k"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201105815"},{"key":"e_1_2_2_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201105815"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3065446"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja210388g"},{"key":"e_1_2_2_48_1","unstructured":"For gold asymmetric catalysis see recent reviews:"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00929D"},{"key":"e_1_2_2_50_2","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1142\/9781848168534_0012","volume-title":"Gold Catalysis An Homogeneous Approch, Vol.\u200513","author":"Toullec P. 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Additional efforts to optimize this reaction are underway."},{"key":"e_1_2_2_55_1","unstructured":"Additional data to manifest the effects of solvents phosphoric acids and silver salts on asymmetric [3+2]-annulations are provided in the Supporting Information Tables\u2005S2 S3 and Eqs.\u2005(s1) (s2)."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202012611","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202012611","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202012611","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,3]],"date-time":"2023-09-03T00:00:39Z","timestamp":1693699239000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202012611"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,15]]},"references-count":62,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2021,2,23]]}},"alternative-id":["10.1002\/anie.202012611"],"URL":"https:\/\/doi.org\/10.1002\/anie.202012611","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,15]]},"assertion":[{"value":"2020-09-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-01-15","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}