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Herein, we report a general process converting a range of ketone derivatives into \u03b1\u2010cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non\u2010classical carbocations.<\/jats:p>","DOI":"10.1002\/anie.202007439","type":"journal-article","created":{"date-parts":[[2020,8,28]],"date-time":"2020-08-28T14:02:18Z","timestamp":1598623338000},"page":"18208-18212","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["An \u03b1\u2010Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung"],"prefix":"10.1002","volume":"59","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3376-343X","authenticated-orcid":false,"given":"Adriano","family":"Bauer","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6123-4543","authenticated-orcid":false,"given":"Giovanni","family":"Di Mauro","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jing","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Tohoku University  Aoba-ku 980-8578 Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3643-0718","authenticated-orcid":false,"given":"Nuno","family":"Maulide","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,8,17]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00890a018"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197902393"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19790910404"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196510752"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19650772405"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18390310312"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197300811"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19730850208"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197606391"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19760882103"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs15333e"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.3998\/ark.5550190.0014.207"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1973-22262"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19600930621"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01273a001"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00799a023"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19495640102"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/jr9320001875"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19850002667"},{"key":"e_1_2_2_16_1","first-page":"3435","author":"Hall A.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02480D"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004374"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004374"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.05.146"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)01094-9"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)81699-3"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol203183k"},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2031882"},{"key":"e_1_2_2_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201600246"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201800521"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00547"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781118909911.ch7"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.3998\/ark.5550190.0010.101"},{"key":"e_1_2_2_29_1","volume-title":"Hypervalent Iodine Chemistry","author":"Zhdankin V. 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