{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:28:53Z","timestamp":1786976933730,"version":"build-2736575974"},"reference-count":118,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,12,28]],"date-time":"2023-12-28T00:00:00Z","timestamp":1703721600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["1R01GM132200-01"],"award-info":[{"award-number":["1R01GM132200-01"]}],"id":[{"id":"10.13039\/100000057","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":[[2024,2,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Alkenes are an important class of organic molecules found among synthetic intermediates and bioactive compounds. They are commonly synthesized through stoichiometric Wittig\u2010type olefination of carbonyls and imines, using ylides or their equivalents. Despite the importance of Wittig\u2010type olefination reactions, their catalytic variants remain underdeveloped. We explored the use of transition metal catalysis to form ylide equivalents from readily available starting materials. Our investigation led to a new copper\u2010catalyzed olefination of imines with alkenyl boronate esters as coupling partners. We identified a heterobimetallic complex, obtained by hydrocupration of the alkenyl boronate esters, as the key catalytic intermediate that serves as an ylide equivalent. The high\n                    <jats:italic>E<\/jats:italic>\n                    \u2010selectivity observed in the reaction is due to the stereoselective addition of this intermediate to an imine, followed by stereospecific anti\u2010elimination.\n                  <\/jats:p>","DOI":"10.1002\/anie.202316521","type":"journal-article","created":{"date-parts":[[2023,12,15]],"date-time":"2023-12-15T13:53:05Z","timestamp":1702648385000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Stereoselective Copper\u2010Catalyzed Olefination of Imines"],"prefix":"10.1002","volume":"63","author":[{"given":"James E.","family":"Baumann","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Washington  109 Bagley Hall 98195 Seattle WA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Crystal P.","family":"Chung","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Washington  109 Bagley Hall 98195 Seattle WA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3615-3423","authenticated-orcid":false,"given":"Gojko","family":"Lalic","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Washington  109 Bagley Hall 98195 Seattle WA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,12,28]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac196409020271"},{"key":"e_1_2_6_3_2","first-page":"1","volume-title":"Topics in Stereochemistry","author":"Schlosser M.","year":"1970"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja910238f"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60105f"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201500475"},{"key":"e_1_2_6_7_2","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1016\/bs.alkal.2020.02.002","volume-title":"The Alkaloids: Chemistry and Biology, Vol.\u200584","author":"Heravi M. 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