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This iridium\/chiral phosphoric acid cooperative catalytic system operates through an atom\u2010economical borrowing hydrogen amination\/aza\u2010Michael cascade, and converts readily available phenylenediamines and racemic allylic alcohols to 1,5\u2010tetrahydrobenzodiazepines in high enantioselectivity. An intriguing solvent\u2010dependent switch of diastereoselectivity was also observed. Mechanistic studies suggested a dynamic kinetic resolution process involving racemization through a reversible Michael addition, making the last step of asymmetric imine reduction the enantiodetermining step of this cascade process.<\/jats:p>","DOI":"10.1002\/anie.202410351","type":"journal-article","created":{"date-parts":[[2024,9,21]],"date-time":"2024-09-21T10:25:03Z","timestamp":1726914303000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Dynamic Asymmetric Diamination of Allylic Alcohols through Borrowing Hydrogen Catalysis: Diastereo\u2010Divergent Synthesis of Tetrahydrobenzodiazepines"],"prefix":"10.1002","volume":"63","author":[{"given":"Yufeng","family":"Liu","sequence":"first","affiliation":[{"name":"Joint School of National University of Singapore and Tianjin University International Campus of Tianjin University  Binhai New City 350207 Fuzhou China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Republic of Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng","family":"Ji","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore and Tianjin University International Campus of Tianjin University  Binhai New City 350207 Fuzhou China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Republic of Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gongfeng","family":"Zou","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore and Tianjin University International Campus of Tianjin University  Binhai New City 350207 Fuzhou China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Republic of Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongbing","family":"Liu","sequence":"additional","affiliation":[{"name":"Hebei Key Laboratory of Organic Functional Molecules College of Chemistry and Material Science Hebei Normal University  050024 Shijiazhuang China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin\u2010Miao","family":"Yang","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore and Tianjin University International Campus of Tianjin University  Binhai New City 350207 Fuzhou China"},{"name":"State Key Laboratory of Applied Organic Chemistry Lanzhou University  730000 Lanzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2944-1315","authenticated-orcid":false,"given":"Yu","family":"Zhao","sequence":"additional","affiliation":[{"name":"Joint School of National University of Singapore and Tianjin University International Campus of Tianjin University  Binhai New City 350207 Fuzhou China"},{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 117543 Singapore Republic of Singapore"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,2]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"For selected general reviews on allylic alcohol transformations see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1560396"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202200126"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.4c00094"},{"key":"e_1_2_3_5_1","unstructured":"For selected reviews on asymmetric allylic substitution of allylic alcohols:"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00144G"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00209"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00506"},{"key":"e_1_2_3_9_1","unstructured":"For selected reports of asymmetric functionalization of alkene in allylic alcohols see:"},{"key":"e_1_2_3_10_2","first-page":"1","volume":"48","author":"Katsuki T.","year":"1996","journal-title":"Org. React."},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03356"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00164"},{"key":"e_1_2_3_13_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307295"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b01102"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-018-0207-1"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009754"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02614"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202203244"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202112993"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202206517"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315325"},{"key":"e_1_2_3_23_1","unstructured":"For selected reviews on general borrowing hydrogen processes see:"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00496E"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00340"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00306"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.1c00125"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c01133"},{"key":"e_1_2_3_29_1","unstructured":"For a review on industrial synthesis using borrowing hydrogen see:"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.5b00199"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/op200174k"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.9b00364"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.3c02803"},{"key":"e_1_2_3_34_1","unstructured":"For selected reviews on enantioselective borrowing hydrogen 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see:"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307789"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02212"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02959"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c02468"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202101517"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-023-00264-z"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aac9283"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201708949"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711126"},{"key":"e_1_2_3_52_1","unstructured":"\u00a0"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201703704"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906199"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202212528"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09958"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-25268-1"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202106514"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600698"},{"key":"e_1_2_3_60_1","unstructured":"For ketone synthesis via borrowing hydrogen involving an Aldol condensation\/olefination process 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stereo-genic centers see:"},{"key":"e_1_2_3_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060312n"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c01242"},{"key":"e_1_2_3_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c05087"},{"key":"e_1_2_3_76_1","unstructured":"For selected reports on the significance of this class of heterocycle see:"},{"key":"e_1_2_3_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm9005548"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.04.017"},{"key":"e_1_2_3_79_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2RA06045K"},{"key":"e_1_2_3_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ml500411h"},{"key":"e_1_2_3_81_1","unstructured":"For selected enantioselective synthesis of this heterocycles see:"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2009.05.039"},{"key":"e_1_2_3_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100938"},{"key":"e_1_2_3_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200309"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601611"},{"key":"e_1_2_3_86_2","first-page":"310","volume":"49","author":"Borrmann R.","year":"2017","journal-title":"Synthesis"},{"key":"e_1_2_3_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800648"},{"key":"e_1_2_3_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c03064"},{"key":"e_1_2_3_89_1","unstructured":"For selected reviews on synergistic catalysis with stereodivergency see:"},{"key":"e_1_2_3_90_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00247A"},{"key":"e_1_2_3_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202210086"},{"key":"e_1_2_3_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00216"},{"key":"e_1_2_3_93_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.checat.2022.10.031"},{"key":"e_1_2_3_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c06267"},{"key":"e_1_2_3_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00639"},{"key":"e_1_2_3_96_1","unstructured":"For selected reviews on stereoselective asymmetric reductive amination see"},{"key":"e_1_2_3_97_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00300C"},{"key":"e_1_2_3_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c04208"},{"key":"e_1_2_3_99_2","first-page":"261","author":"Wang C.","year":"2023","journal-title":"Top. Curr. Chem."},{"key":"e_1_2_3_100_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00391D"},{"key":"e_1_2_3_101_1","unstructured":"For selected key examples see:"},{"key":"e_1_2_3_102_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503062"},{"key":"e_1_2_3_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja057222n"},{"key":"e_1_2_3_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9021683"},{"key":"e_1_2_3_105_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100878"},{"key":"e_1_2_3_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201606063"},{"key":"e_1_2_3_107_1","unstructured":"For representative examples reporting solvent-dependent diastereo-divergent reactions see:"},{"key":"e_1_2_3_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b06227"},{"key":"e_1_2_3_109_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201601188"},{"key":"e_1_2_3_110_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711873"},{"key":"e_1_2_3_111_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202016941"},{"key":"e_1_2_3_112_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c03148"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202410351","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202410351","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202410351","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,2,15]],"date-time":"2026-02-15T09:41:03Z","timestamp":1771148463000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202410351"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,2]]},"references-count":112,"journal-issue":{"issue":"49","published-print":{"date-parts":[[2024,12,2]]}},"alternative-id":["10.1002\/anie.202410351"],"URL":"https:\/\/doi.org\/10.1002\/anie.202410351","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,2]]},"assertion":[{"value":"2024-06-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202410351"}}