{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T03:55:44Z","timestamp":1788926144706,"version":"build-2803163510"},"reference-count":107,"publisher":"Wiley","issue":"31","license":[{"start":{"date-parts":[[2026,5,29]],"date-time":"2026-05-29T00:00:00Z","timestamp":1780012800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,5,29]],"date-time":"2026-05-29T00:00:00Z","timestamp":1780012800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22471080"],"award-info":[{"award-number":["22471080"]}],"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":["22163007"],"award-info":[{"award-number":["22163007"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003453","name":"Natural Science Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2025A1515012079"],"award-info":[{"award-number":["2025A1515012079"]}],"id":[{"id":"10.13039\/501100003453","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005329","name":"Natural Science Foundation of Guizhou Province","doi-asserted-by":"publisher","award":["ZSYS[2025]033"],"award-info":[{"award-number":["ZSYS[2025]033"]}],"id":[{"id":"10.13039\/501100005329","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005329","name":"Natural Science Foundation of Guizhou Province","doi-asserted-by":"publisher","award":["KJZY[2025]073"],"award-info":[{"award-number":["KJZY[2025]073"]}],"id":[{"id":"10.13039\/501100005329","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":[[2026,7,27]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    The development of efficient methods for the diverse synthesis of optically active fused N\u2010heterocycles is vital for advancing medicinal chemistry. Hydrodearomative annulation of weakly reactive azaarenes presents a promising yet challenging strategy to fulfil such a synthetic purpose. Herein, we report a reductive three\u2010component reaction for the construction of fused N\u2010heterocycles with contiguous quaternary and tertiary carbon stereocenters, enabled by a simple chiral phosphoric acid\/PhSiH\n                    <jats:sub>3<\/jats:sub>\n                    catalytic system. A wide variety of isoquinolinium salts were transformed in combination with formaldehyde and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010alkyl anilines into the target products with good isolated yields (up to 88%), and high diastereoselectivities (&gt;20:1 dr) and enantioselectivities (up to 96.5:3.5 er). The reaction proceeds through sequential hydrodearomatization, C\n                    <jats:sub>4<\/jats:sub>\n                    \u2010methylation, and asymmetric annulation, in which the chiral phosphoric acid participates in both the formation of intermediates and the stereocontrolling steps. DFT calculations further reveal that the observed enantioselectivity arises from C\u2013H\u00b7\u00b7\u00b7O interactions between the substrate and catalyst, with steric repulsion effects playing a decisive role.\n                  <\/jats:p>","DOI":"10.1002\/anie.2229634","type":"journal-article","created":{"date-parts":[[2026,5,29]],"date-time":"2026-05-29T12:28:12Z","timestamp":1780057692000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Asymmetric Reductive Three\u2010Component Annulation Reaction for Constructing Fused N\u2010Heterocycles With Contiguous Stereogenic Centers"],"prefix":"10.1002","volume":"65","author":[{"given":"Guang\u2010Peng","family":"Lu","sequence":"first","affiliation":[{"name":"Key Lab of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology  Guangzhou P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4355-0294","authenticated-orcid":false,"given":"Huan\u2010Feng","family":"Jiang","sequence":"additional","affiliation":[{"name":"Key Lab of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology  Guangzhou P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng\u2010Gang","family":"Ci","sequence":"additional","affiliation":[{"name":"Guizhou Provincial Key Laboratory of Green Catalysis and Materials for Resource Conversion Department of Chemistry and Chemical Engineering Qiannan Normal University for Nationalities  Duyun P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierre H.","family":"Dixneuf","sequence":"additional","affiliation":[{"name":"University of Rennes  Rennes France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7023-8781","authenticated-orcid":false,"given":"Min","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Lab of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology  Guangzhou P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,5,29]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40362\u2010013\u20100014\u20107"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.1c00251"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c01786"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm901241e"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00196A"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10593\u2010012\u20100960\u2010z"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0353762"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802237"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902570"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2023042"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC04386C"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC04712A"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00312"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812647"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201909919"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04838"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c01353"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.023.202202601"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c13618"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204236"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b00085"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202013540"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4GC00506F"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701158"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204179"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06060A"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201900907"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202305449"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200328h"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar500146e"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00564"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03958"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00138G"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00082E"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00496"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.2c00550"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00764"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c09794"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c13618"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.07.021"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm900723w"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100307m"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00567"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c02573"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202505060"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c09827"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c00394"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.023.202303085"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c02776"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b09038"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010025\u201009607\u20106"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c12015"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c03915"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c12069"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c02773"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202507798"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202514300"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202512405"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202422951"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202410581"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202305450"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202316454"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202212976"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010023\u201001097\u2010x"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010023\u201001384\u2010x"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c14589"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c01489"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c00414"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202505167"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202519340"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202300419"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202300481"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202200371"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010023\u201039134\u20109"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202515020"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202319289"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407752"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c10123"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c04924"},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c01623"},{"key":"e_1_2_8_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c12466"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c03552"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202510078"},{"key":"e_1_2_8_86_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202514155"},{"key":"e_1_2_8_87_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202410351"},{"key":"e_1_2_8_88_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob05870c"},{"key":"e_1_2_8_89_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600191"},{"key":"e_1_2_8_90_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b06009"},{"key":"e_1_2_8_91_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c14200"},{"key":"e_1_2_8_92_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja211684v"},{"key":"e_1_2_8_93_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701158"},{"key":"e_1_2_8_94_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701484"},{"key":"e_1_2_8_95_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201705746"},{"key":"e_1_2_8_96_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03285"},{"key":"e_1_2_8_97_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1182826"},{"key":"e_1_2_8_98_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010023\u201039134\u20109"},{"key":"e_1_2_8_99_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010018\u20100178\u20105"},{"key":"e_1_2_8_100_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201908857"},{"key":"e_1_2_8_101_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja973892k"},{"key":"e_1_2_8_102_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja980139y"},{"key":"e_1_2_8_103_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC00127F"},{"key":"e_1_2_8_104_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202400143"},{"key":"e_1_2_8_105_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5c05041"},{"key":"e_1_2_8_106_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b10152"},{"key":"e_1_2_8_107_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja205891m"},{"key":"e_1_2_8_108_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303430"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.2229634","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.2229634","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.2229634","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T13:38:39Z","timestamp":1785245919000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.2229634"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5,29]]},"references-count":107,"journal-issue":{"issue":"31","published-print":{"date-parts":[[2026,7,27]]}},"alternative-id":["10.1002\/anie.2229634"],"URL":"https:\/\/doi.org\/10.1002\/anie.2229634","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5,29]]},"assertion":[{"value":"2026-01-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-23","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-29","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e2229634"}}