{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T23:20:07Z","timestamp":1791415207781,"version":"4.3.3"},"reference-count":124,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2023,9,15]],"date-time":"2023-09-15T00:00:00Z","timestamp":1694736000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE-2042353"],"award-info":[{"award-number":["CHE-2042353"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["GM147523-01"],"award-info":[{"award-number":["GM147523-01"]}],"id":[{"id":"10.13039\/100000002","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":[[2023,10,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report herein a Cu\u2010catalyzed regio\u2010, diastereo\u2010 and enantioselective acylboration of 1,3\u2010butadienylboronate with acyl fluorides. Under the developed conditions, the reactions provide (<jats:italic>Z<\/jats:italic>)\u2010\u03b2,\u03b3\u2010unsaturated ketones bearing an \u03b1\u2010tertiary stereocenter with high <jats:italic>Z<\/jats:italic>\u2010selectivity and excellent enantioselectivities. While direct access to highly enantioenriched <jats:italic>E<\/jats:italic>\u2010isomers was not successful, we showed that such molecules can be synthesized with excellent <jats:italic>E<\/jats:italic>\u2010selectivity and optical purities via Pd\u2010catalyzed alkene isomerization from the corresponding <jats:italic>Z<\/jats:italic>\u2010isomers. The orthogonal chemical reactivities of the functional groups embedded in the ketone products allow for diverse chemoselective transformations, which provides a valuable platform for further derivatization.<\/jats:p>","DOI":"10.1002\/anie.202304796","type":"journal-article","created":{"date-parts":[[2023,9,15]],"date-time":"2023-09-15T10:52:19Z","timestamp":1694775139000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Copper\u2010Catalyzed Asymmetric Acylboration of 1,3\u2010Butadienylboronate with Acyl Fluorides"],"prefix":"10.1002","volume":"62","author":[{"given":"Shang","family":"Gao","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Auburn University  36849 Auburn AL USA"},{"name":"Department of Medicinal Chemistry, School of Pharmacy China Pharmaceutical University  210009 Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiaming","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Auburn University  36849 Auburn AL USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Diego","family":"Troya","sequence":"additional","affiliation":[{"name":"Department of Chemistry Virginia Tech  24061 Blacksburg VA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9841-8274","authenticated-orcid":false,"given":"Ming","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Auburn University  36849 Auburn AL USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,9,15]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For selected reviews:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306945"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306788"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr8002533"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900096x"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100371y"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00620"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00075"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00831"},{"key":"e_1_2_7_10_1","unstructured":"For selected reviews:"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00213"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC06460B"},{"key":"e_1_2_7_13_1","unstructured":"For selected reviews:"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3GC40997J"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC02148K"},{"key":"e_1_2_7_16_1","unstructured":"\u00a0"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1219274"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja311208a"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3110544"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4087193"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605001"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b04024"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12760"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c00019"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c07230"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c04237"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c00488"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c04060"},{"key":"e_1_2_7_29_1","unstructured":"\u00a0"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja801213x"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805356j"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809610h"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja511640g"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09333"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12307"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b13300"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b06957"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b07600"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c01420"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c06144"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c11843"},{"key":"e_1_2_7_42_1","unstructured":"\u00a0"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0608904"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0693183"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja800997j"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9048493"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001188"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja500268w"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b09346"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b13812"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c08319"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09486"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c06245"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c08912"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09306"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c12779"},{"key":"e_1_2_7_57_1","unstructured":"For a recent perspective see:"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04767"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10149"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b01784"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b09721"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201911008"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c01260"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09118"},{"key":"e_1_2_7_65_1","unstructured":"For selected recent reviews see:"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.05.077"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.02.027"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00816C"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c02758"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201607493"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707323"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201903174"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b01911"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC02905B"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC03531A"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC04787E"},{"key":"e_1_2_7_77_1","unstructured":"For selected reviews on metal-catalyzed carbonyl addition see:"},{"key":"e_1_2_7_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078340r"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802938"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aah5133"},{"key":"e_1_2_7_81_1","unstructured":"\u00a0"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01399"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201801080"},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02653"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC00226J"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00461"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01535"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03819"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04089"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02657"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03366"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000039"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c04107"},{"key":"e_1_2_7_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c02086"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c02831"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03628"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC04047B"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202006420"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202107004"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC04058H"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202208908"},{"key":"e_1_2_7_102_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201902805"},{"key":"e_1_2_7_103_1","unstructured":"\u00a0"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.34.1075"},{"key":"e_1_2_7_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302539s"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.6b00200"},{"key":"e_1_2_7_107_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol301563g"},{"key":"e_1_2_7_108_1","unstructured":"For selected references on catalytic diene protoboration see:"},{"key":"e_1_2_7_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja909640b"},{"key":"e_1_2_7_110_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300443"},{"key":"e_1_2_7_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03483"},{"key":"e_1_2_7_112_1","unstructured":"\u00a0"},{"key":"e_1_2_7_113_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01565a041"},{"key":"e_1_2_7_114_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198205553"},{"key":"e_1_2_7_115_1","unstructured":"For an overview of boron-stabilized carbanions see:"},{"key":"e_1_2_7_116_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527210793358259"},{"key":"e_1_2_7_117_2","doi-asserted-by":"publisher","DOI":"10.1021\/om060131u"},{"key":"e_1_2_7_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/om070103r"},{"key":"e_1_2_7_119_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja505455z"},{"key":"e_1_2_7_120_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00098a009"},{"key":"e_1_2_7_121_1","unstructured":"For a review on the Curtin\u2013Hammett principle:"},{"key":"e_1_2_7_122_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00054a001"},{"key":"e_1_2_7_123_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.217.4558.401"},{"key":"e_1_2_7_124_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00240a025"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/anie.202304796","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202304796","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,7,24]],"date-time":"2025-07-24T15:18:34Z","timestamp":1753370314000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202304796"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,9,15]]},"references-count":124,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2023,10,23]]}},"alternative-id":["10.1002\/anie.202304796"],"URL":"https:\/\/doi.org\/10.1002\/anie.202304796","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,9,15]]},"assertion":[{"value":"2023-04-04","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-09-15","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202304796"}}