{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T19:53:28Z","timestamp":1790366008392,"version":"4.1.0"},"reference-count":56,"publisher":"Wiley","issue":"39","license":[{"start":{"date-parts":[[2025,8,21]],"date-time":"2025-08-21T00:00:00Z","timestamp":1755734400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,8,21]],"date-time":"2025-08-21T00:00:00Z","timestamp":1755734400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100000770","name":"University Of Manchester","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000770","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/W016354\/1"],"award-info":[{"award-number":["EP\/W016354\/1"]}],"id":[{"id":"10.13039\/501100000266","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":[[2025,9,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Cross\u2010coupling strategies involving strain release have gained significant recent attention for the construction of complex molecular frameworks, particularly in the context of preparing bioisosteres for medicinal chemistry. While the reactivity of cyclopropanes and bicyclo[1.1.0]butanes (BCBs) has been extensively studied, higher homologues are emerging as valuable substrates for synthesis. For example, methods for the fragmentation and coupling of bicyclo[2.1.0]pentane, or housane, ketones show promise but are currently limited in substrate scope. Here, we describe a mild, atom\u2010economical, samarium diiodide (Sml\n                    <jats:sub>2<\/jats:sub>\n                    )\u2010catalyzed fragmentation and coupling of alkyl and aryl housane ketones with alkenes that grants access to functionalized norbornane structural motifs, not easily accessible by classical cycloaddition approaches, and with considerable potential for further manipulation.\n                  <\/jats:p>","DOI":"10.1002\/anie.202512018","type":"journal-article","created":{"date-parts":[[2025,7,8]],"date-time":"2025-07-08T10:19:56Z","timestamp":1751969996000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["SmI\n                    <sub>2<\/sub>\n                    \u2010Catalyzed Coupling of Alkyl Housane Ketones and Alkenes in an Approach to Norbornanes"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1266-1493","authenticated-orcid":false,"given":"Debayan","family":"Roy","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8933-2199","authenticated-orcid":false,"given":"Jack I.","family":"Mansell","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8125-3293","authenticated-orcid":false,"given":"Giorgia","family":"Barison","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"},{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 Padova 35131 Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5693-7773","authenticated-orcid":false,"given":"Song","family":"Yu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rocco","family":"Katavic","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7957-2316","authenticated-orcid":false,"given":"Ciro","family":"Romano","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0293-5742","authenticated-orcid":false,"given":"Nikolas","family":"Kaltsoyannis","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3179-2509","authenticated-orcid":false,"given":"David J.","family":"Procter","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manchester  Oxford Road Manchester M13 9PL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,8,21]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202213003"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO01741B"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-022-00811-3"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c08206"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309886"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00014"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c03073"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202402730"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adh9737"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01135-y"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c14276"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c05067"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b01372"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2020.112617"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.09.072"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm100959g"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.04.004"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB00621J"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol901990c"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4RA07989B"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710846"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-54117-0"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr60301a002"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo4002867"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.4c00857"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo070190x"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202314700"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-018-0219-x"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c01356"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-024-01438-8"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5c00469"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja962331a"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00263-3"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo9820667"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol050256f"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0506258"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/cs400587s"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b13119"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03723"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adp5777"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c10053"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c05414"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c14845"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo300135v"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00358A"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1992-21544"},{"key":"e_1_2_8_48_1","unstructured":"CCDC 2454073 2454076 2454079 2454177 and 2455063 contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre."},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.4c01996"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202401120"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00746"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.1c01215"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202303859"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108270191012544"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03314"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO00148F"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202512018","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202512018","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202512018","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,2,11]],"date-time":"2026-02-11T19:23:55Z","timestamp":1770837835000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202512018"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,8,21]]},"references-count":56,"journal-issue":{"issue":"39","published-print":{"date-parts":[[2025,9,22]]}},"alternative-id":["10.1002\/anie.202512018"],"URL":"https:\/\/doi.org\/10.1002\/anie.202512018","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,8,21]]},"assertion":[{"value":"2025-06-02","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-04","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202512018"}}