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The type of migration was controlled by the catalyst, with rhodium(II) and copper(II) delivering \u03b1\u2010acyloxy acrylates from 2,3\u2010acyloxy migration, while silver(I) catalyzed the formation of regioisomeric \u03b2\u2010acyloxy acrylates through 1,2\u2010hydride migration. In addition to the good yields observed for 2,3\u2010acyloxy migrations (56\u201395\u2009%), the reactions exhibited remarkable chemo\u2010, regio\u2010 and diastereoselectivity. The\n                    <jats:italic>E\u2009<\/jats:italic>\n                    :\u2009Z ratio was found to be excellent for Rh (20\u2009:\u20091 or higher in most cases) and moderate to good for Cu (6\u201313\u2009:\u20091 favoring\n                    <jats:italic>E<\/jats:italic>\n                    \u2010isomer). In the case of Ag\u2010catalyzed 1,2\u2010hydride migration, the yield (60\u201393\u2009%) and diastereoselectivity (7\u2009:\u20091 to &gt;20\u2009:\u20091 favoring\n                    <jats:italic>Z<\/jats:italic>\n                    isomer) for \u03b2\u2010acyloxy acrylates were also high, although the competitive formation of regioisomeric \u03b1\u2010acyloxy acrylate was detected in minor amounts. Furthermore, both 1,2\u2010hydride and 2,3\u2010acyloxy migrations showed tolerance to functional groups, which were successfully explored in subsequent post\u2010functionalization processes to access heterocyclic nuclei of pharmacological relevance. We also investigated the rhodium\u2010catalyzed 2,3\u2010acyloxy migration, with the support of computational chemistry, to unravel this reaction mechanism and to explain the factors influencing migratory assistance and diastereoselectivity.\n                  <\/jats:p>","DOI":"10.1002\/asia.202401745","type":"journal-article","created":{"date-parts":[[2025,2,14]],"date-time":"2025-02-14T12:53:38Z","timestamp":1739537618000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Regiodivergent Synthesis of \u03b1\u2010 and \u03b2\u2010Acyloxy Acrylates through Catalyst\u2010Driven Migrations from \u03b1\u2010Diazo\u2010\u03b2\u2010Acyloxy Esters"],"prefix":"10.1002","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0009-0007-3702-4160","authenticated-orcid":false,"given":"Gabriela M.","family":"Diogo","sequence":"first","affiliation":[{"name":"MESOLab (Laboratory of Methodology and Synthetic Organic Chemistry) Departamento de Qu\u00edmica Universidade Federal de Santa Catarina  88040-900 Florian\u00f3polis-SC Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3928-9599","authenticated-orcid":false,"given":"Pedro A. M.","family":"Moro","sequence":"additional","affiliation":[{"name":"MESOLab (Laboratory of Methodology and Synthetic Organic Chemistry) Departamento de Qu\u00edmica Universidade Federal de Santa Catarina  88040-900 Florian\u00f3polis-SC Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2044-914X","authenticated-orcid":false,"given":"Vinicius C.","family":"Port","sequence":"additional","affiliation":[{"name":"GEEMM (Molecular Electronic Structure and Materials Group) Departamento de Qu\u00edmica Universidade Federal de Santa Catarina  88040-900 Florian\u00f3polis-SC Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6276-8539","authenticated-orcid":false,"given":"Amanda K.","family":"Jacobs","sequence":"additional","affiliation":[{"name":"GEEMM (Molecular Electronic Structure and Materials Group) Departamento de Qu\u00edmica Universidade Federal de Santa Catarina  88040-900 Florian\u00f3polis-SC Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6455-7831","authenticated-orcid":false,"given":"Giovanni F.","family":"Caramori","sequence":"additional","affiliation":[{"name":"GEEMM (Molecular Electronic Structure and Materials Group) Departamento de Qu\u00edmica Universidade Federal de Santa Catarina  88040-900 Florian\u00f3polis-SC Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9189-1624","authenticated-orcid":false,"given":"Marcus M.","family":"S\u00e1","sequence":"additional","affiliation":[{"name":"MESOLab (Laboratory of Methodology and Synthetic Organic Chemistry) Departamento de Qu\u00edmica Universidade Federal de Santa Catarina  88040-900 Florian\u00f3polis-SC Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,2,24]]},"reference":[{"key":"e_1_2_10_1_1","unstructured":"\u00a0"},{"key":"e_1_2_10_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00872H"},{"key":"e_1_2_10_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c10204"},{"key":"e_1_2_10_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c09873"},{"key":"e_1_2_10_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC02086J"},{"key":"e_1_2_10_6_1","unstructured":"\u00a0"},{"key":"e_1_2_10_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00121"},{"key":"e_1_2_10_8_2","first-page":"3233","volume":"11","author":"Mix K. 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