{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T17:54:00Z","timestamp":1792605240460,"version":"4.5.0"},"reference-count":111,"publisher":"Wiley","issue":"34","license":[{"start":{"date-parts":[[2023,6,20]],"date-time":"2023-06-20T00:00:00Z","timestamp":1687219200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004869","name":"Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004869","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":[[2023,8,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Design, synthesis and application of benzene bioisosteres have attracted a lot of attention in the past 20\u2005years. Recently, bicyclo[2.1.1]hexanes have emerged as highly attractive bioisosteres for <jats:italic>ortho<\/jats:italic>\u2010 and <jats:italic>meta<\/jats:italic>\u2010substituted benzenes. Herein we report a mild, scalable and transition\u2010metal\u2010free protocol for the construction of highly substituted bicyclo[2.1.1]hexan\u20102\u2010ones through Lewis acid catalyzed (3+2)\u2010cycloaddition of bicyclo[1.1.0]\u2010butane ketones with disubstituted ketenes. The reaction shows high functional group tolerance as documented by the successful preparation of various 3\u2010alkyl\u20103\u2010aryl as well as 3,3\u2010bisalkyl bicyclo[2.1.1]hexan\u20102\u2010ones (26\u2005examples, up to 89\u2009% yield). Postfunctionalization of the exocyclic ketone moiety is also demonstrated.<\/jats:p>","DOI":"10.1002\/anie.202304771","type":"journal-article","created":{"date-parts":[[2023,5,11]],"date-time":"2023-05-11T12:19:13Z","timestamp":1683807553000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":194,"title":["Lewis Acid Catalyzed Formal (3+2)\u2010Cycloaddition of Bicyclo[1.1.0]butanes with Ketenes"],"prefix":"10.1002","volume":"62","author":[{"given":"Niklas","family":"Radhoff","sequence":"first","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Constantin G.","family":"Daniliuc","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1706-513X","authenticated-orcid":false,"given":"Armido","family":"Studer","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Westf\u00e4lische Wilhelms-Universit\u00e4t  Corrensstra\u00dfe 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,6,20]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"For selected reviews and perspectives 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see:"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608116"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol503300m"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.10.057"},{"key":"e_1_2_3_26_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-33827-3"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-05290-z"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09733"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000548"},{"key":"e_1_2_3_31_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202004183"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2108881118"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00786-z"},{"key":"e_1_2_3_35_1","unstructured":"\u00a0"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC03948F"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c02976"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-04636-x"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01135-y"},{"key":"e_1_2_3_40_1","unstructured":"For selected examples 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see:"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101230"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3005263"},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.24820\/ark.5550190.p009.634"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00491-5"},{"key":"e_1_2_3_68_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.05.079"},{"key":"e_1_2_3_69_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90545-9"},{"key":"e_1_2_3_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00087a005"},{"key":"e_1_2_3_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.08.028"},{"key":"e_1_2_3_72_1","unstructured":"For selected examples of O-nucleophiles see:"},{"key":"e_1_2_3_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961333a"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01164-9"},{"key":"e_1_2_3_75_1","unstructured":"For selected examples of N-nucleophiles see:"},{"key":"e_1_2_3_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01555"},{"key":"e_1_2_3_77_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-30817-3"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00200a038"},{"key":"e_1_2_3_79_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC07134C"},{"key":"e_1_2_3_80_1","unstructured":"For selected examples of C-nucleophiles see:"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00305a012"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)86664-8"},{"key":"e_1_2_3_83_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(98)00927-9"},{"key":"e_1_2_3_84_1","unstructured":"For 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see:"},{"key":"e_1_2_3_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0391208"},{"key":"e_1_2_3_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901290z"},{"key":"e_1_2_3_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460698"},{"key":"e_1_2_3_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00365a030"},{"key":"e_1_2_3_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00211a039"},{"key":"e_1_2_3_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0492900"},{"key":"e_1_2_3_97_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar030055g"},{"key":"e_1_2_3_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0172525"},{"key":"e_1_2_3_100_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3103007"},{"key":"e_1_2_3_102_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB01837D"},{"key":"e_1_2_3_103_1","unstructured":"For 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These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202304771","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,21]],"date-time":"2023-08-21T16:57:56Z","timestamp":1692637076000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202304771"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,6,20]]},"references-count":111,"journal-issue":{"issue":"34","published-print":{"date-parts":[[2023,8,21]]}},"alternative-id":["10.1002\/anie.202304771"],"URL":"https:\/\/doi.org\/10.1002\/anie.202304771","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,6,20]]},"assertion":[{"value":"2023-04-04","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-06-20","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202304771"}}