{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T13:11:59Z","timestamp":1788441119595,"version":"build-2803163510"},"reference-count":88,"publisher":"American Chemical Society (ACS)","issue":"42","license":[{"start":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T00:00:00Z","timestamp":1760400000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T00:00:00Z","timestamp":1760400000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T00:00:00Z","timestamp":1760400000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100013066","name":"Key Scientific Research Project of Colleges and Universities in Henan Province","doi-asserted-by":"publisher","award":["19A150004"],"award-info":[{"award-number":["19A150004"]}],"id":[{"id":"10.13039\/501100013066","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013066","name":"Key Scientific Research Project of Colleges and Universities in Henan Province","doi-asserted-by":"publisher","award":["24A150026"],"award-info":[{"award-number":["24A150026"]}],"id":[{"id":"10.13039\/501100013066","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013066","name":"Key Scientific Research Project of Colleges and Universities in Henan Province","doi-asserted-by":"publisher","award":["26A150033"],"award-info":[{"award-number":["26A150033"]}],"id":[{"id":"10.13039\/501100013066","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100009101","name":"Education Department of Henan Province","doi-asserted-by":"publisher","award":["2024GGJS113"],"award-info":[{"award-number":["2024GGJS113"]}],"id":[{"id":"10.13039\/501100009101","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21372112"],"award-info":[{"award-number":["21372112"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100017700","name":"Henan Provincial Science and Technology Research Project","doi-asserted-by":"publisher","award":["242102320123"],"award-info":[{"award-number":["242102320123"]}],"id":[{"id":"10.13039\/501100017700","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2025,10,24]]},"DOI":"10.1021\/acs.joc.5c01927","type":"journal-article","created":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T03:32:56Z","timestamp":1760499176000},"page":"15031-15045","source":"Crossref","is-referenced-by-count":1,"title":["Ir-f-Amphbinol-Catalyzed Asymmetric Hydrogenation of\n                    <i>N<\/i>\n                    -Protected \u03b1-Amino Ketones Followed by Deprotection for Preparation of \u03b2-Primary Amino Alcohols"],"prefix":"10.1021","volume":"90","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9872-2460","authenticated-orcid":true,"given":"Weilong","family":"Wu","sequence":"first","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wanyang","family":"Chen","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenzhi","family":"Mo","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ning","family":"Qiu","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yueru","family":"Hao","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaolei","family":"Ge","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feng","family":"Zhang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bingqing","family":"Liu","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongsheng","family":"Deng","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Zhou","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6795-6205","authenticated-orcid":true,"given":"Baoming","family":"Ji","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials","place":["Luoyang, P. R. China"]},{"name":"Luoyang Normal University","place":["Luoyang, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,10,14]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b03889"},{"key":"ref2\/cit2a","doi-asserted-by":"publisher","DOI":"10.1021\/jo970032d"},{"key":"ref2\/cit2b","doi-asserted-by":"publisher","DOI":"10.2165\/00003088-200140010-00003"},{"key":"ref2\/cit2c","doi-asserted-by":"publisher","DOI":"10.2165\/11539240-000000000-00000"},{"key":"ref2\/cit2d","doi-asserted-by":"publisher","DOI":"10.1002\/ddr.430320105"},{"key":"ref2\/cit2e","doi-asserted-by":"publisher","DOI":"10.1016\/0140-6736(90)93099-B"},{"key":"ref2\/cit2f","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2044.2002.02324.x"},{"key":"ref3\/cit3a","unstructured":"aZacch\u00e8, M.; Gatti, P. A.; Gerli, F.; Sbarbada, D.; Rondina, F. A process for the preparation of enantiomerically pure norepinephrine. WO 2020212157 A1."},{"key":"ref3\/cit3b","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202200490"},{"key":"ref3\/cit3c","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)87372-5"},{"key":"ref3\/cit3d","doi-asserted-by":"publisher","DOI":"10.1021\/ja01186a024"},{"key":"ref4\/cit4a","doi-asserted-by":"publisher","DOI":"10.1021\/op970128+"},{"key":"ref4\/cit4b","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcatb.2013.07.021"},{"key":"ref4\/cit4c","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.09.013"},{"key":"ref4\/cit4d","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcata.2012.06.042"},{"key":"ref5\/cit5a","doi-asserted-by":"publisher","DOI":"10.1055\/s-1970-21628"},{"key":"ref5\/cit5b","doi-asserted-by":"publisher","DOI":"10.1021\/jo00001a084"},{"key":"ref5\/cit5c","doi-asserted-by":"publisher","DOI":"10.1016\/j.gresc.2021.09.002"},{"key":"ref5\/cit5d","doi-asserted-by":"publisher","DOI":"10.1055\/s-1997-1004"},{"key":"ref5\/cit5e","doi-asserted-by":"publisher","DOI":"10.1021\/ja901058u"},{"key":"ref5\/cit5f","doi-asserted-by":"publisher","DOI":"10.1097\/00005344-198809000-00010"},{"key":"ref5\/cit5g","doi-asserted-by":"publisher","DOI":"10.1016\/S0026-895X(25)11117-6"},{"key":"ref6\/cit6a","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.12.077"},{"key":"ref6\/cit6b","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)77244-3"},{"key":"ref6\/cit6c","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.7b00261"},{"key":"ref7\/cit7a","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200463075"},{"key":"ref7\/cit7b","doi-asserted-by":"publisher","DOI":"10.1021\/om9807405"},{"key":"ref7\/cit7c","doi-asserted-by":"publisher","DOI":"10.1021\/cr00013a004"},{"key":"ref7\/cit7d","doi-asserted-by":"publisher","DOI":"10.1021\/cr000411y"},{"key":"ref7\/cit7e","doi-asserted-by":"publisher","DOI":"10.1021\/cr9500038"},{"key":"ref8\/cit8a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812968"},{"key":"ref8\/cit8b","doi-asserted-by":"publisher","DOI":"10.1021\/ol500699c"},{"key":"ref8\/cit8c","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC04131A"},{"key":"ref8\/cit8d","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO01443A"},{"key":"ref8\/cit8e","doi-asserted-by":"publisher","DOI":"10.1038\/nature17191"},{"key":"ref8\/cit8f","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c01162"},{"key":"ref8\/cit8g","doi-asserted-by":"publisher","DOI":"10.1021\/ja054401w"},{"key":"ref8\/cit8h","doi-asserted-by":"publisher","DOI":"10.1021\/ja0677012"},{"key":"ref8\/cit8i","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(03)00022-3"},{"key":"ref9\/cit9a","doi-asserted-by":"publisher","DOI":"10.1021\/ja00171a036"},{"key":"ref9\/cit9b","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00807-2"},{"key":"ref9\/cit9c","doi-asserted-by":"publisher","DOI":"10.1021\/ja0432113"},{"key":"ref9\/cit9d","doi-asserted-by":"publisher","DOI":"10.1021\/ar700100e"},{"key":"ref9\/cit9e","doi-asserted-by":"publisher","DOI":"10.1021\/jo802339t"},{"key":"ref10\/cit10a","doi-asserted-by":"publisher","DOI":"10.1021\/ja039153n"},{"key":"ref10\/cit10b","doi-asserted-by":"publisher","DOI":"10.1021\/ol901605a"},{"key":"ref10\/cit10c","doi-asserted-by":"publisher","DOI":"10.1021\/ol0474812"},{"key":"ref10\/cit10d","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702491"},{"key":"ref10\/cit10e","doi-asserted-by":"publisher","DOI":"10.1021\/jo00090a026"},{"key":"ref10\/cit10f","doi-asserted-by":"publisher","DOI":"10.1021\/ja001098k"},{"key":"ref11\/cit11a","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700594"},{"key":"ref11\/cit11b","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00212"},{"key":"ref11\/cit11c","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)00274-4"},{"key":"ref11\/cit11d","doi-asserted-by":"publisher","DOI":"10.1021\/ja00210a070"},{"key":"ref12\/cit12a","doi-asserted-by":"publisher","DOI":"10.1021\/ol051007u"},{"key":"ref12\/cit12b","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.02.055"},{"key":"ref12\/cit12c","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35333D"},{"key":"ref13\/cit13a","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378891"},{"key":"ref13\/cit13b","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO00237H"},{"key":"ref14\/cit14a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102710"},{"key":"ref14\/cit14b","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201000716"},{"key":"ref14\/cit14c","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00693D"},{"key":"ref14\/cit14d","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-39375-8"},{"key":"ref15\/cit15a","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c02274"},{"key":"ref15\/cit15b","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2024.110037"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00524"},{"key":"ref17\/cit17a","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202300367"},{"key":"ref17\/cit17b","doi-asserted-by":"publisher","DOI":"10.1021\/ja511422q"},{"key":"ref17\/cit17c","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.4c00045"},{"key":"ref18\/cit18a","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1611533"},{"key":"ref18\/cit18b","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01828"},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c06179"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1055\/s-1991-20699"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b00079"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1021\/cs2004467"},{"key":"ref23\/cit23","unstructured":"Tuttle, R. R.; Browne, C. E. 1-(3,4-dihydroxyphenyl)-2-(4-(4-hydroxyphenyl)butaylamino)ethanol. US Patent 5,395,970A, 1995."},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1016\/j.rechem.2023.100843"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.07.052"},{"key":"ref26\/cit26a","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.2c02358"},{"key":"ref26\/cit26b","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b03862"},{"key":"ref26\/cit26c","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201604855"},{"key":"ref26\/cit26d","doi-asserted-by":"publisher","DOI":"10.3390\/molecules29163743"},{"key":"ref26\/cit26e","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03550"},{"key":"ref26\/cit26f","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5c00943"},{"key":"ref27\/cit27","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c00986"},{"key":"ref28\/cit28","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111689"},{"key":"ref29\/cit29","doi-asserted-by":"publisher","DOI":"10.1002\/chin.200444087"},{"key":"ref30\/cit30","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.02.027"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.5c01927","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.5c01927","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,24]],"date-time":"2025-10-24T08:12:49Z","timestamp":1761293569000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.5c01927"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,10,14]]},"references-count":88,"journal-issue":{"issue":"42","published-print":{"date-parts":[[2025,10,24]]}},"alternative-id":["10.1021\/acs.joc.5c01927"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.5c01927","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,10,14]]}}}