{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T21:27:41Z","timestamp":1790630861791,"version":"4.1.0"},"reference-count":90,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2025,11,23]],"date-time":"2025-11-23T00:00:00Z","timestamp":1763856000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,11,23]],"date-time":"2025-11-23T00:00:00Z","timestamp":1763856000000},"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":["U22A20378"],"award-info":[{"award-number":["U22A20378"]}],"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":["22422103"],"award-info":[{"award-number":["22422103"]}],"id":[{"id":"10.13039\/501100001809","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":[[2026,1,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The construction of stereogenic S(VI) centers remains a formidable challenge in asymmetric catalysis, despite incremental advances. The enantioselective transformation of racemic sulfonimidoyl chlorides is rarely described for forming chiral S(VI)\u2500O bonds and limited to covalent organocatalytic manners. Herein, we report the first chiral Lewis acid catalyzed asymmetric nucleophilic substitution of sulfonimidoyl chlorides, using 2\u2010hydroxypyridines as nucleophiles, affording sulfur(VI)\u2010stereogenic chiral sulfonimidate esters with good yields (up to 94% yield), excellent chemoselectivities (\n                    <jats:italic>O<\/jats:italic>\n                    \u2010functionalization) and high enantioselectivities (up to 99% ee). Enantioenriched sulfonimidate esters are stereospecifically transformed into chiral S(VI) derivatives, with the 2\u2010hydroxypyridine unit acting as the leaving group. The practicality of this method is enhanced via a directed one\u2010pot procedure of in situ\u2010generated sulfonimidoyl chloride from S(IV) sulfonamide. Furthermore, the addition of quinuclidine as an additive can trigger rapid racemization of sulfonimidoyl chloride, establishing a dynamic kinetic process instead of a kinetic resolution. Mechanistic studies indicate that the reaction proceeds via an S\n                    <jats:sub>N<\/jats:sub>\n                    2 pathway with kinetic resolution characteristics. A bifunctional activation mode is elucidated by mechanistic experiments and density functional theory calculations, in which Zn(II)\u2010ligand complex activates the sulfonimidoyl chloride, while imidazolidine N\u2013H forms a H\u2010bond with the nitrogen atom in 2\u2010hydroxypyridines.\n                  <\/jats:p>","DOI":"10.1002\/anie.202521905","type":"journal-article","created":{"date-parts":[[2025,11,24]],"date-time":"2025-11-24T06:39:36Z","timestamp":1763966376000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Zn(II)\u2010Catalyzed Enantioselective Nucleophilic Substitution Reactions: Access to Sulfur(VI)\u2010Stereogenic Sulfonimidate Esters"],"prefix":"10.1002","volume":"65","author":[{"given":"Sai\u2010Ya","family":"Lian","sequence":"first","affiliation":[{"name":"State Key Laboratory of Antiviral Drugs Pingyuan Laboratory Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ning","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Antiviral Drugs Pingyuan Laboratory Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7039-0479","authenticated-orcid":false,"given":"Yin","family":"Tian","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Southwestern Chinese Medicine Resources School of Pharmacy Chengdu University of Traditional Chinese, Medicine  Chengdu 611137 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4113-2168","authenticated-orcid":false,"given":"Ming\u2010Sheng","family":"Xie","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Antiviral Drugs Pingyuan Laboratory Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0629-4524","authenticated-orcid":false,"given":"Hai\u2010Ming","family":"Guo","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Antiviral Drugs Pingyuan Laboratory Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,23]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302209"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201610456"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.09.091"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00960"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2020.112885"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1080\/17460441.2021.1948008"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202201993"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00002"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC02614C"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202302059"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.2c00626"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c10486"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5c01027"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202500170"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957\u20104166(97)00046\u20103"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1186\/1860\u20105397\u20103\u201033"},{"key":"e_1_2_8_17_1","first-page":"3827","volume":"23","author":"Pandey A.","year":"2011","journal-title":"Synthesis"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201303850"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b00143"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810887"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810472"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904543"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c03111"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c04431"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c03966"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC04299H"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c03531"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205341"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c00962"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202217130"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202319871"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c00266"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c04798"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO01749H"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010025\u201057251\u20105"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201800273"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202109160"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c06674"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407114"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c00374"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202506929"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5SC01270H"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c13758"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415873"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00749a085"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01327a002"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/00404\u20100399(50)1195N\u2010"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201915519"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00761"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207456"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c03473"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2024.02.016"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202500170"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/ceur.202500006"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309399"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201900440"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000108"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c01099"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202300536"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202406915"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00149a001"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA14056G"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202316702"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010024\u201001452\u2010w"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c09937"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202510595"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.adx2509"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-38059-7"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c02546"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c02072"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010024\u201052419\u2010x"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC06334A"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202416741"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)01975\u20104"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja005866j"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja100265j"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201410782"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1016\/0010\u20108545(94)01117\u2010T"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja511622e"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000632"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00769"},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01032a028"},{"key":"e_1_2_8_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0209969"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp057101"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601607"},{"key":"e_1_2_8_86_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic5003594"},{"key":"e_1_2_8_87_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja507202f"},{"key":"e_1_2_8_88_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00384a017"},{"key":"e_1_2_8_89_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002265"},{"key":"e_1_2_8_90_1","unstructured":"Deposition Numbers 2484877 (for3aa) 2484869 (for10aa) and 2484868 (for4au) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinforma tionszentrum Karlsruhe Access Structures service."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202521905","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202521905","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202521905","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,9]],"date-time":"2026-04-09T14:50:47Z","timestamp":1775746247000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202521905"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,11,23]]},"references-count":90,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2026,1,16]]}},"alternative-id":["10.1002\/anie.202521905"],"URL":"https:\/\/doi.org\/10.1002\/anie.202521905","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,11,23]]},"assertion":[{"value":"2025-10-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-16","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-23","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e21905"}}