{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T17:47:08Z","timestamp":1784310428414,"version":"3.55.0"},"reference-count":77,"publisher":"Wiley","issue":"42","license":[{"start":{"date-parts":[[2023,9,12]],"date-time":"2023-09-12T00:00:00Z","timestamp":1694476800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100018992","name":"Fonds der Chemischen Industrie","doi-asserted-by":"publisher","award":["Liebig Fellowship"],"award-info":[{"award-number":["Liebig Fellowship"]}],"id":[{"id":"10.13039\/100018992","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100018992","name":"Fonds der Chemischen Industrie","doi-asserted-by":"publisher","award":["Ph.D. Fellowship"],"award-info":[{"award-number":["Ph.D. Fellowship"]}],"id":[{"id":"10.13039\/100018992","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Emmy Noether Programme, STO 1175\/3-1"],"award-info":[{"award-number":["Emmy Noether Programme, STO 1175\/3-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005713","name":"Technische Universit\u00e4t M\u00fcnchen","doi-asserted-by":"publisher","award":["TUM Junior Fellow Programme"],"award-info":[{"award-number":["TUM Junior Fellow Programme"]}],"id":[{"id":"10.13039\/501100005713","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":[[2023,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Catalytic desaturations are important strategies for the functionalization of organic molecules. In nature, flavoenzymes mediate the formation of \u03b1,\u03b2\u2010unsaturated carbonyl compounds by concomitant cofactor reduction. Contrary to many laboratory methods for these reactions, such as the <jats:italic>Saegusa<\/jats:italic>\u2010<jats:italic>Ito<\/jats:italic> oxidation, no transition metal reagents or catalysts are required. However, a molecular flavin\u2010mediated variant has not been reported so far. We disclose a photochemical approach for silyl enol ether oxidation, which leads to \u03b1,\u03b2\u2010unsaturated ketones (13 examples) in very good yields. The flavin catalysts are stable throughout the desaturation reaction, and we successfully applied them in a subsequent aerobic epoxidation by simply changing the reaction conditions. This protocol allowed us to directly convert silyl enol ethers into \u03b1,\u03b2\u2010epoxyketones in a one\u2010pot fashion (12 examples). Sequential flavin catalysis is not limited to one specific reactivity combination and can, <jats:italic>inter alia<\/jats:italic>, couple the photochemical oxidation with radical additions. We anticipate that flavin\u2010catalyzed desaturation will be applicable to other substrate classes and that its sequential catalytic activity will enable rapid substrate diversification.<\/jats:p>","DOI":"10.1002\/anie.202310634","type":"journal-article","created":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T07:41:16Z","timestamp":1693208476000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Photochemical Desaturation and Epoxidation with Oxygen by Sequential Flavin Catalysis"],"prefix":"10.1002","volume":"62","author":[{"given":"Alexandra","family":"Walter","sequence":"first","affiliation":[{"name":"School of Natural Sciences and Catalysis Research Center (CRC) Technical University of Munich (TUM)  Lichtenbergstr. 4 85747 Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wolfgang","family":"Eisenreich","sequence":"additional","affiliation":[{"name":"School of Natural Sciences and Catalysis Research Center (CRC) Technical University of Munich (TUM)  Lichtenbergstr. 4 85747 Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6747-3035","authenticated-orcid":false,"given":"Golo","family":"Storch","sequence":"additional","affiliation":[{"name":"School of Natural Sciences and Catalysis Research Center (CRC) Technical University of Munich (TUM)  Lichtenbergstr. 4 85747 Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,9,12]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2NP20069D"},{"key":"e_1_2_3_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0703092"},{"key":"e_1_2_3_3_1","unstructured":"\u00a0"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201403275"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1055\/a-1458-2419"},{"key":"e_1_2_3_6_1","unstructured":"Examples of multiple activity of flavin catalysts:"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b12081"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00052"},{"key":"e_1_2_3_9_1","unstructured":"For reviews on general catalytic desaturation see:"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900202j"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr1003503"},{"key":"e_1_2_3_12_2","doi-asserted-by":"crossref","unstructured":"C. Wen T. Li Z. Huang Q.-K. Kang Chem. Rec.2023 e202300146 https:\/\/doi.org\/10.1002\/tcr.202300146.","DOI":"10.1002\/tcr.202300146"},{"key":"e_1_2_3_13_1","unstructured":"\u00a0"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/a806930a"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi401529y"},{"key":"e_1_2_3_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm301848w"},{"key":"e_1_2_3_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00399a052"},{"key":"e_1_2_3_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo047858h"},{"key":"e_1_2_3_19_1","unstructured":"Examples using palladium catalysts:"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050284y"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja206575j"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja403165u"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo302465v"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02243"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201811197"},{"key":"e_1_2_3_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-017-02381-8"},{"key":"e_1_2_3_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja001825b"},{"key":"e_1_2_3_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc46778c"},{"key":"e_1_2_3_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00640-2"},{"key":"e_1_2_3_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja990908t"},{"key":"e_1_2_3_31_1","unstructured":"For the flavin-mediated reverse (reduction) reaction see:"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja053976q"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo801588d"},{"key":"e_1_2_3_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00650"},{"key":"e_1_2_3_35_1","unstructured":"\u00a0"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja301386g"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2093212"},{"key":"e_1_2_3_38_1","unstructured":"\u00a0"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja026663t"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5074646"},{"key":"e_1_2_3_41_1","unstructured":"Examples:"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2888"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906293"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03422"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202212158"},{"key":"e_1_2_3_46_1","unstructured":"Photochemical reactions via single-electron oxidation of silyl enol ethers:"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10641-y"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03697"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202101352"},{"key":"e_1_2_3_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04384"},{"key":"e_1_2_3_51_1","unstructured":"\u00a0"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19870000075"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00843a043"},{"key":"e_1_2_3_54_1","unstructured":"Examples by C\u2212C bond formation:"},{"key":"e_1_2_3_55_2","first-page":"0101","volume":"1","author":"Ebel H.","year":"2003","journal-title":"Synthesis"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01155"},{"key":"e_1_2_3_57_1","unstructured":"Examples by alcohol 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Chemie International 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