{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T19:44:40Z","timestamp":1791402280453,"version":"4.3.3"},"reference-count":120,"publisher":"Wiley","issue":"46","license":[{"start":{"date-parts":[[2023,10,12]],"date-time":"2023-10-12T00:00:00Z","timestamp":1697068800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2023,10,12]],"date-time":"2023-10-12T00:00:00Z","timestamp":1697068800000},"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":["22071139, 22371150"],"award-info":[{"award-number":["22071139, 22371150"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004608","name":"Natural Science Foundation of Jiangsu Province","doi-asserted-by":"publisher","award":["BK20180892"],"award-info":[{"award-number":["BK20180892"]}],"id":[{"id":"10.13039\/501100004608","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012246","name":"Priority Academic Program Development of Jiangsu Higher Education Institutions","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100012246","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":[[2023,11,13]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Catalytic asymmetric methods for the synthesis of synthetically versatile P\u2010stereogenic building blocks offer an efficient and practical approach for the diversity\u2010oriented preparation of P\u2010chiral phosphorus compounds. Herein, we report the first nickel\u2010catalyzed synthesis of P\u2010stereogenic secondary aminophosphine\u2010boranes by the asymmetric addition of primary phosphines to azo compounds. We further demonstrate that the P\u2212H and P\u2212N bonds on these phosphanyl hydrazine building blocks can be reacted sequentially and stereospecifically to access various P\u2010stereogenic compounds with structural diversity.<\/jats:p>","DOI":"10.1002\/anie.202313112","type":"journal-article","created":{"date-parts":[[2023,9,28]],"date-time":"2023-09-28T22:40:56Z","timestamp":1695940856000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Nickel\u2010Catalyzed Asymmetric Synthesis of P\u2010Stereogenic Phosphanyl Hydrazine Building Blocks"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9576-8589","authenticated-orcid":false,"given":"Chuanyong","family":"Wang","sequence":"first","affiliation":[{"name":"College of Chemistry and Chemical Engineering Yangzhou University  180 Siwangting Road 225002 Yangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qingliang","family":"Yang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Yangzhou University  180 Siwangting Road 225002 Yangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuan\u2010Hao","family":"Dai","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Yangzhou University  180 Siwangting Road 225002 Yangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianqi","family":"Xiong","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Yangzhou University  180 Siwangting Road 225002 Yangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Zheng","sequence":"additional","affiliation":[{"name":"Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and Materials College of Chemical Engineering Nanjing Forestry University  210037 Nanjing P.\u2005R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei\u2010Liang","family":"Duan","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Yangzhou University  180 Siwangting Road 225002 Yangzhou China"},{"name":"College of Chemistry and Chemical Engineering Inner Mongolia University  235 West University Street 010021 Hohhot China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,10,12]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00460a018"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00087a006"},{"key":"e_1_2_3_4_2","volume-title":"Phosphorus Ligands in Asymmetric Catalysis, Synthesis and Applications","author":"B\u00f6rner A.","year":"2008"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00081"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00029"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00075"},{"key":"e_1_2_3_8_1","unstructured":"\u00a0"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm701260b"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt.3948"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202011527"},{"key":"e_1_2_3_12_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00029a009"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2006.05.009"},{"key":"e_1_2_3_15_2","volume-title":"P-Stereogenic Ligands in Enantioselective Catalysis","author":"Grabu-losa A.","year":"2011"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00031B"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000406"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00633"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2023.215192"},{"key":"e_1_2_3_20_1","unstructured":"For selected examples using chiral auxiliary strategy for the synthesis of P(III)-stereogenic phosphines see:"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)97063-1"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39930000531"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800065"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja200988c"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja400208t"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC07504A"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC01944K"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b01180"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c03336"},{"key":"e_1_2_3_30_1","unstructured":"\u00a0"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973423i"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200208)2002:15<2535::AID-EJOC2535>3.0.CO;2-O"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja053458f"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja209700j"},{"key":"e_1_2_3_35_1","unstructured":"\u00a0"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020503)41:9<1612::AID-ANIE1612>3.0.CO;2-H"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200400690"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1145229"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805094j"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja903880q"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02277"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00734"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-19807-5"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c02745"},{"key":"e_1_2_3_45_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-991077"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc01939a"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.gresc.2020.12.002"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.6023\/A20010002"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.checat.2022.09.048"},{"key":"e_1_2_3_51_1","unstructured":"For selected examples of asymmetric catalytic synthesis of P-stereogenic phosphine oxides see:"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja512029x"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500201"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201807749"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.9b00216"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b04570"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02982"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b00860"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200805066"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800144"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11938"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009358"},{"key":"e_1_2_3_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04041J"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC00091A"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC01049A"},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09334"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.10.048"},{"key":"e_1_2_3_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202117093"},{"key":"e_1_2_3_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202301628"},{"key":"e_1_2_3_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202111137"},{"key":"e_1_2_3_71_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-023-1678-1"},{"key":"e_1_2_3_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303727"},{"key":"e_1_2_3_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202306511"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-37987-8"},{"key":"e_1_2_3_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202300011"},{"key":"e_1_2_3_76_1","unstructured":"\u00a0"},{"key":"e_1_2_3_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0267324"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058096q"},{"key":"e_1_2_3_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/om061116s"},{"key":"e_1_2_3_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800534k"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/om900800z"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058100y"},{"key":"e_1_2_3_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9014887"},{"key":"e_1_2_3_84_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC05841C"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202117760"},{"key":"e_1_2_3_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c04112"},{"key":"e_1_2_3_87_2","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00123-3"},{"key":"e_1_2_3_88_1","unstructured":"\u00a0"},{"key":"e_1_2_3_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja501007t"},{"key":"e_1_2_3_90_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4QO00017J"},{"key":"e_1_2_3_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic202472f"},{"key":"e_1_2_3_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/om300405h"},{"key":"e_1_2_3_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c00539"},{"key":"e_1_2_3_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09654"},{"key":"e_1_2_3_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c05649"},{"key":"e_1_2_3_96_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527834204"},{"key":"e_1_2_3_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c02772"},{"key":"e_1_2_3_98_1","unstructured":"\u00a0"},{"key":"e_1_2_3_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c00181"},{"key":"e_1_2_3_100_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.abp8488"},{"key":"e_1_2_3_101_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202307450"},{"key":"e_1_2_3_102_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202111957"},{"key":"e_1_2_3_103_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO01819A"},{"key":"e_1_2_3_104_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01210"},{"key":"e_1_2_3_105_1","unstructured":"The addition product decomposed during the purification by silica gel chromatography."},{"key":"e_1_2_3_106_1","unstructured":"Deposition number2287304 (for2\u2009m)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_3_107_1","unstructured":"The alkylation with retention of configuration at phosphorus see:"},{"key":"e_1_2_3_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973685k"},{"key":"e_1_2_3_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2034816"},{"key":"e_1_2_3_110_1","unstructured":"The arylation with retention of configuration at phosphorus see:"},{"key":"e_1_2_3_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00036a054"},{"key":"e_1_2_3_112_2","doi-asserted-by":"publisher","DOI":"10.1002\/hc.520030519"},{"key":"e_1_2_3_113_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01636-6"},{"key":"e_1_2_3_114_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0003605"},{"key":"e_1_2_3_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja029404c"},{"key":"e_1_2_3_116_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC05340F"},{"key":"e_1_2_3_117_1","unstructured":"The configurations of compounds5\u2009aand5\u2009bwere assigned asRandS respectively. Please see the Supporting Information for more details."},{"key":"e_1_2_3_118_1","doi-asserted-by":"crossref","unstructured":"K.\u2005D. Troev Chapter\u20052\u2014Reactivity of P\u2212H Group of Phosphines. In Reactivity of P\u2212H Group of Phosphorus Based Compounds; Academic Press: Cambridge MA USA 2018 19\u2013144.","DOI":"10.1016\/B978-0-12-813834-2.00002-0"},{"key":"e_1_2_3_119_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2019.130819"},{"key":"e_1_2_3_120_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(01)00236-1"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202313112","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202313112","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202313112","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T07:38:55Z","timestamp":1769845135000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202313112"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,10,12]]},"references-count":120,"journal-issue":{"issue":"46","published-print":{"date-parts":[[2023,11,13]]}},"alternative-id":["10.1002\/anie.202313112"],"URL":"https:\/\/doi.org\/10.1002\/anie.202313112","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,10,12]]},"assertion":[{"value":"2023-09-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-10-12","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202313112"}}