{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,4]],"date-time":"2026-03-04T21:28:31Z","timestamp":1772659711067,"version":"3.50.1"},"reference-count":39,"publisher":"Wiley","issue":"39","license":[{"start":{"date-parts":[[2024,6,21]],"date-time":"2024-06-21T00:00:00Z","timestamp":1718928000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004238","name":"Universit\u00e4t Potsdam","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004238","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":[[2024,9,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Birch reductions are well\u2010known transformations of arenes, applied for large scale synthesis of 1,4\u2010cyclohexadienes. Herein, we describe first reactions of benzoic acids in the presence of carbonyl compounds, affording aldol products in moderate to high yields. Alkyl aldehydes give the expected nonconjugated dienes by reaction at the \u03b1\u2010position. Interestingly, the intermediately formed enolate attacks aryl aldehydes and ketones from its \u03b3\u2010position, which can be explained by steric hindrance. This opens the door for the one\u2010pot synthesis of 1,3\u2010cyclohexadienes, which are not accessible by classical Birch reductions. Our method is applicable to benzoic, <jats:italic>m<\/jats:italic>\u2010 and <jats:italic>p<\/jats:italic>\u2010toluic acid and various carbonyl compounds, and more than 25 new products were isolated in up to 93\u2009% yield. Prochiral aryl aldehydes afford diastereomeric mixtures in ratios of about 4\u2009:\u20091, but in the cyclohexadiene ring only <jats:italic>trans<\/jats:italic> isomers are formed with high selectivity. Finally, the 1,3\u2010cyclohexadienes are suitable precursors for further transformations, which we have demonstrated in first examples. Thus, aromatization affords products of a formal <jats:italic>meta<\/jats:italic> selective Friedel\u2013Crafts alkylation, and four new stereocenters were generated by cycloaddition of singlet oxygen with excellent selectivity.<\/jats:p>","DOI":"10.1002\/anie.202407568","type":"journal-article","created":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T02:14:55Z","timestamp":1715652895000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["One\u2010Pot Synthesis of 1,3\u2010Cyclohexadienes by Birch Reduction in the Presence of Carbonyl Compounds"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2230-7698","authenticated-orcid":false,"given":"Tobias","family":"Kr\u00fcger\u2010Braunert","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Potsdam  Karl-Liebknecht-Str. 24\u201325 D-14476 Potsdam\/Golm Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3576-7426","authenticated-orcid":false,"given":"Torsten","family":"Linker","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Potsdam  Karl-Liebknecht-Str. 24\u201325 D-14476 Potsdam\/Golm Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,6,21]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/qr9500400069"},{"key":"e_1_2_3_2_1","first-page":"1","volume":"42","author":"Rabideau P. 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