{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T09:23:35Z","timestamp":1790501015910,"version":"4.1.0"},"reference-count":94,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2022,4,5]],"date-time":"2022-04-05T00:00:00Z","timestamp":1649116800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2021YFF0701600"],"award-info":[{"award-number":["2021YFF0701600"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22031004"],"award-info":[{"award-number":["22031004"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21921003"],"award-info":[{"award-number":["21921003"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21901043"],"award-info":[{"award-number":["21901043"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003399","name":"Science and Technology Commission of Shanghai Municipality","doi-asserted-by":"publisher","award":["21ZR1445900"],"award-info":[{"award-number":["21ZR1445900"]}],"id":[{"id":"10.13039\/501100003399","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003395","name":"Shanghai Municipal Education Commission","doi-asserted-by":"publisher","award":["20212308"],"award-info":[{"award-number":["20212308"]}],"id":[{"id":"10.13039\/501100003395","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":[[2022,6,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>\u03b3\u2010Butenolide and \u03b3\u2010butyrolactone scaffolds are two types of important core structures in numerous natural products and bioactive targets. However, methods to construct the chiral quaternary arylated \u03b3\u2010butenolide are rarely explored. We herein report an efficient Pd\u2010catalyzed enantioselective \u03b3\u2010arylation of \u03b2,\u03b3\u2010unsaturated butenolides with aryl bromides, which shows high \u03b3\u2010selectivity, good functional group tolerance and excellent enantioselectivity. Notably, this protocol also allows for facile construction of tricyclic tetrahydroindolines and tetrahydroisoquinolinones in one step. DFT calculations are consistent with the experimental results, suggesting that the \u03b3\u2010arylation is favoured over the \u03b1\u2010arylation. Finally, this method is applied to the rapid synthesis of natural product (<jats:italic>R<\/jats:italic>)\u2010(+)\u2010boivinianin\u2005A.<\/jats:p>","DOI":"10.1002\/anie.202202046","type":"journal-article","created":{"date-parts":[[2022,3,22]],"date-time":"2022-03-22T14:18:17Z","timestamp":1647958697000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Palladium\u2010Catalyzed Enantioselective \u03b3\u2010Arylation of \u03b2,\u03b3\u2010Unsaturated Butenolides"],"prefix":"10.1002","volume":"61","author":[{"given":"Sanliang","family":"Li","sequence":"first","affiliation":[{"name":"Department of Chemistry Fudan University  2005 Songhu Road Shanghai 200438 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiaoyu","family":"Chen","sequence":"additional","affiliation":[{"name":"Academy for Engineering and Technology Fudan University  2005 Songhu Road Shanghai 200438 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junfeng","family":"Yang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Fudan University  2005 Songhu Road Shanghai 200438 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4636-2846","authenticated-orcid":false,"given":"Junliang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Fudan University  2005 Songhu Road Shanghai 200438 China"},{"name":"School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,4,5]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","unstructured":"C.Maul M.Przewosny W.Englberger(Gruenenthal GmbH Germany) WO2003004483A1 2003;"},{"key":"e_1_2_7_3_2","unstructured":"C.Maul B.Sundermann M.Przewosny H.-H.Hennies(Gruenenthal GmbH Germany) WO2003004016A1 2003;"},{"key":"e_1_2_7_4_2","unstructured":"S.Runyon Y.Zhang C.Hassler B.Gilmour(Research Triangle Institute USA) WO2013086200A1 2013;"},{"key":"e_1_2_7_5_2","unstructured":"S.Runyon Y.Zhang C.Hassler B.Gilmour(Research Triangle Institute USA) US9150582B2 2015;"},{"key":"e_1_2_7_6_2","unstructured":"A.Ziemniak John T.Hopper Allen T.Pugliese Peter(OXIS INT INC) 1999\/03\/08\/Application date 1999."},{"key":"e_1_2_7_7_1","unstructured":"\u00a0"},{"key":"e_1_2_7_8_2","first-page":"524","volume":"52","author":"Chamorro G.","year":"2002","journal-title":"Arzneim.-Forsch."},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4274(02)00482-4"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1515\/acph-2017-0014"},{"key":"e_1_2_7_11_1","unstructured":"\u00a0"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(98)00487-9"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1007534416561"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(02)01354-5"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00044-010-9438-7"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bse.2005.11.005"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/np200008g"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0921-3449(99)00047-6"},{"key":"e_1_2_7_19_1","unstructured":"\u00a0"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202486"},{"key":"e_1_2_7_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202486"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206368"},{"key":"e_1_2_7_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206368"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201905993"},{"key":"e_1_2_7_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201905993"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700437"},{"key":"e_1_2_7_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700437"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00521"},{"key":"e_1_2_7_25_1","unstructured":"For selected reviews and examples see:"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60303a004"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.2174\/1389557511313060007"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00151"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00346K"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC02295D"},{"key":"e_1_2_7_31_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0201106"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1087673"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04480"},{"key":"e_1_2_7_35_1","unstructured":"\u00a0"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200194y"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc50806d"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202010682"},{"key":"e_1_2_7_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202010682"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol9007102"},{"key":"e_1_2_7_40_1","unstructured":"\u00a0"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704529"},{"key":"e_1_2_7_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704529"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01908"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202106109"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202106109"},{"key":"e_1_2_7_44_1","unstructured":"\u00a0"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017545t"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300481"},{"key":"e_1_2_7_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300481"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201913136"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201913136"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201401067"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201401067"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201912408"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201912408"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201907840"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201907840"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904948"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200904948"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00029"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203898"},{"key":"e_1_2_7_54_1","unstructured":"\u00a0"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/om0611498"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC02742C"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03262"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03223"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-019-0278-7"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202010598"},{"key":"e_1_2_7_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202010598"},{"key":"e_1_2_7_61_1","unstructured":"\u00a0"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01214"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10365"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804318"},{"key":"e_1_2_7_64_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201804318"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711845"},{"key":"e_1_2_7_65_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711845"},{"key":"e_1_2_7_66_1","unstructured":"Deposition Number2112909 (for3d)contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503210"},{"key":"e_1_2_7_68_1","unstructured":"\u00a0"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c05346"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b03203"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01768"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-0428-1"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/om200945q"},{"key":"e_1_2_7_74_1","unstructured":"\u00a0"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9409804"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00484"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403446"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC01221F"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202202046","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202202046","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202202046","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,24]],"date-time":"2023-08-24T13:31:32Z","timestamp":1692883892000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202202046"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,5]]},"references-count":94,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2022,6,7]]}},"alternative-id":["10.1002\/anie.202202046"],"URL":"https:\/\/doi.org\/10.1002\/anie.202202046","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,5]]},"assertion":[{"value":"2022-02-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-04-05","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202202046"}}