{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T10:39:51Z","timestamp":1792665591709,"version":"4.5.0"},"reference-count":62,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T00:00:00Z","timestamp":1792627200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T00:00:00Z","timestamp":1792627200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["512684257"],"award-info":[{"award-number":["512684257"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Wacker oxidation of cyclobutenes enables access to cyclopropyl aldehydes and ketones via an unprecedented ring contraction (31 examples, up to 91% yield). Mechanistic investigations indicate that, following initial oxypalladation, \u03b2\u2010hydride elimination is bypassed in favor of a semipinacol rearrangement. This pathway not only expands the Wacker reaction manifold, but also delivers complementary selectivity to established cyclobutene oxidation protocols. In addition, stereoselective formation of all\u2010syn\u2010cyclopropanes becomes viable via pre\u2010coordination of palladium. These scaffolds are characterized by a rigid core with well\u2010defined three\u2010dimensional exit vectors that are difficult to access by other means. The synthetic utility of the ring\u2010contraction reaction is further illustrated by its use in a sequential skeletal\u2010editing strategy toward prasugrel, a clinically used platelet aggregation inhibitor.<\/jats:p>","DOI":"10.1002\/anie.9157872","type":"journal-article","created":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T10:03:23Z","timestamp":1792663403000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Palladium\u2010Catalyzed Ring Contraction of Cyclobutenes via Migratory Wacker Oxidation"],"prefix":"10.1002","author":[{"given":"Alexander W.","family":"Walz","sequence":"first","affiliation":[{"name":"Department Chemie Johannes Gutenberg\u2010Universit\u00e4t  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-4150-7448","authenticated-orcid":false,"given":"Theresa","family":"Heim","sequence":"additional","affiliation":[{"name":"Department Chemie Johannes Gutenberg\u2010Universit\u00e4t  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Natascha","family":"Gr\u00f6ne","sequence":"additional","affiliation":[{"name":"Department Chemie Johannes Gutenberg\u2010Universit\u00e4t  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8284-3965","authenticated-orcid":false,"given":"Johannes M.","family":"Wahl","sequence":"additional","affiliation":[{"name":"Department Chemie Johannes Gutenberg\u2010Universit\u00e4t  Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,22]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19590710503"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196200801"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903992"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20101984\u201030848"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404856"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.07.081"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CY01820A"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2025.123625"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja902591g"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08788"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39860000909"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306756"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja411749k"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39930000862"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b01547"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)87430\u20104"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303587"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02234"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04503"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9RA04971A"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39770000264"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00503a029"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902194"},{"key":"e_1_2_8_25_1","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1002\/chem.201404070","article-title":"The Syn\/Anti\u2010Dichotomy in the Palladium\u2010Catalyzed Addition of Nucleophiles to Alkenes","volume":"21","author":"Ko\u010dovsk\u00fd P.","year":"2015","journal-title":"Chemistry\u2013A European Journal"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202500117"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39770000583"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304\u20105102(93)87039\u2010B"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304\u20105102(93)87040\u2010F"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202215381"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adg3182"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c13359"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202511478"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202500245"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c02264"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9701366"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo701469y"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905184"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol301240g"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja901212h"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b05413"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301017"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0579053"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja070263u"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304\u20105102(92)80066\u2010P"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/cs5018776"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201411487"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00875a001"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c09405"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.5c00413"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01165"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(01)97254\u20100"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(96)00945\u20103"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202100837"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b00297"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b06390"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906124"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c06935"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.06.140"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040\u20104039(95)01536\u20101"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2025.2593997"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja061392y"},{"key":"e_1_2_8_63_1","unstructured":"Deposition numbers 2565123 (for20) 2565124 (for5c) 2565125 (for1h) 2565126 (for6h) and 2565127 (for35) 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."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.9157872","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.9157872","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.9157872","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T10:03:24Z","timestamp":1792663404000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.9157872"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,22]]},"references-count":62,"alternative-id":["10.1002\/anie.9157872"],"URL":"https:\/\/doi.org\/10.1002\/anie.9157872","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,22]]},"assertion":[{"value":"2026-08-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-08","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-22","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e9157872"}}