{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,14]],"date-time":"2026-07-14T01:07:24Z","timestamp":1783991244536,"version":"3.55.0"},"reference-count":18,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2020,10,20]],"date-time":"2020-10-20T00:00:00Z","timestamp":1603152000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Inversions in the periselectivity of formal aza-Diels\u2013Alder cycloadditions between \u03b1-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the \u03b1-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.<\/jats:p>","DOI":"10.3390\/molecules25204811","type":"journal-article","created":{"date-parts":[[2020,10,20]],"date-time":"2020-10-20T20:50:07Z","timestamp":1603227007000},"page":"4811","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Periselectivity in the Aza-Diels\u2013Alder Reaction of 1-Azadienes with \u03b1-Oxoketenes: A Combined Experimental and Theoretical Study"],"prefix":"10.3390","volume":"25","author":[{"given":"Marc","family":"Presset","sequence":"first","affiliation":[{"name":"Aix Marseille Universit\u00e9, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michel","family":"Rajzmann","sequence":"additional","affiliation":[{"name":"Aix Marseille Universit\u00e9, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guillaume","family":"Dauvergne","sequence":"additional","affiliation":[{"name":"Aix Marseille Universit\u00e9, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean","family":"Rodriguez","sequence":"additional","affiliation":[{"name":"Aix Marseille Universit\u00e9, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0646-006X","authenticated-orcid":false,"given":"Yoann","family":"Coquerel","sequence":"additional","affiliation":[{"name":"Aix Marseille Universit\u00e9, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1219","DOI":"10.1055\/s-1994-25673","article-title":"\u03b1-Oxoketenes\u2014Preparation and Chemistry","volume":"1994","author":"Wentrup","year":"1994","journal-title":"Synthesis"},{"key":"ref_2","first-page":"159","article-title":"Ketene cycloadditions","volume":"Volume 45","author":"Paquette","year":"1994","journal-title":"Organic Reactions"},{"key":"ref_3","first-page":"271","article-title":"Acylketenes","volume":"Volume 23","author":"Danheiser","year":"2006","journal-title":"Science of Synthesis: Houben-Weyl Methods of Molecular Transformations"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3022","DOI":"10.1039\/b912599j","article-title":"Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis","volume":"38","author":"Reber","year":"2009","journal-title":"Chem. 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