{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T12:13:48Z","timestamp":1789992828106,"version":"4.0.1"},"reference-count":99,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2022,3,30]],"date-time":"2022-03-30T00:00:00Z","timestamp":1648598400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["81903574"],"award-info":[{"award-number":["81903574"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["2020QNA7001"],"award-info":[{"award-number":["2020QNA7001"]}],"id":[{"id":"10.13039\/501100012226","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":[[2022,6,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In contrast to the well\u2010established [3+2] cycloaddition reactions, the catalytic enantioselective [3+<jats:italic>n<\/jats:italic>] (<jats:italic>n<\/jats:italic>\u22653) cycloaddition reaction of activated isocyanides for the preparation of six\u2010membered or larger ring systems has remained underdeveloped. Herein, we report the first example of highly diastereo\u2010 and enantioselective [3+3] cycloaddition of activated isocyanides with azomethine imines. By employing silver catalysis, a wide range of biologically important bicyclic 1,2,4\u2010triazines were obtained in high yields (up to 99\u2009%) with good to excellent stereoselectivities (up to &gt;20\u2009:\u20091 dr, 99\u2009% ee). In addition, the same catalytic system could be applied to both the late\u2010stage functionalization of complex bioactive molecules and the kinetic resolution of racemic azomethine imines, further highlighting its versatility and synthetic utility.<\/jats:p>","DOI":"10.1002\/anie.202202679","type":"journal-article","created":{"date-parts":[[2022,3,15]],"date-time":"2022-03-15T15:59:36Z","timestamp":1647359976000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":40,"title":["Diastereo\u2010 and Enantioselective Silver\u2010Catalyzed [3+3] Cycloaddition and Kinetic Resolution of Azomethine Imines with Activated Isocyanides"],"prefix":"10.1002","volume":"61","author":[{"given":"Ling\u2010Fei","family":"Tao","sequence":"first","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sen","family":"Zhang","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fen","family":"Huang","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wen\u2010Tao","family":"Wang","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhang\u2010Hong","family":"Luo","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linghui","family":"Qian","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6847-4825","authenticated-orcid":false,"given":"Jia\u2010Yu","family":"Liao","sequence":"additional","affiliation":[{"name":"College of Pharmaceutical Sciences and Hangzhou Institute of Innovative Medicine Zhejiang University  Hangzhou 310058 China"},{"name":"Innovation Institute for Artificial Intelligence in Medicine of Zhejiang University  Hangzhou 310018 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,3,30]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09198G"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c01786"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2021.105076"},{"key":"e_1_2_3_6_2","unstructured":"J.\u2005T. Njardarson \u201cTop 200 Small Molecule Pharmaceuticals by Retail Sales in 2020\u201d can be found under https:\/\/njardarson.lab.arizona.edu\/sites\/njardarson.lab.arizona.edu\/files\/Top%20200\u2009%20Pharmaceuticals%20Small%20Molecule%202020New.pdf 2020."},{"key":"e_1_2_3_7_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00695"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00514"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-021-00321-1"},{"key":"e_1_2_3_11_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196305651"},{"key":"e_1_2_3_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19630751304"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr970324e"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078371m"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr5007182"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202003115"},{"key":"e_1_2_3_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202003115"},{"key":"e_1_2_3_17_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197703393"},{"key":"e_1_2_3_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19770890604"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900411f"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.11.005"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00444J"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000890"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202003224"},{"key":"e_1_2_3_24_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00280a056"},{"key":"e_1_2_3_26_2","first-page":"2191","author":"Xue M.-X.","year":"2009","journal-title":"Synlett"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja110534g"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol103104y"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201411852"},{"key":"e_1_2_3_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201411852"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC00856F"},{"key":"e_1_2_3_31_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo980949s"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301256q"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309719"},{"key":"e_1_2_3_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309719"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404629"},{"key":"e_1_2_3_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201404629"},{"key":"e_1_2_3_36_1","unstructured":"For selected examples see:"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800003"},{"key":"e_1_2_3_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800003"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201100636"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06683A"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812654"},{"key":"e_1_2_3_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201812654"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b00767"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201900481"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202107767"},{"key":"e_1_2_3_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202107767"},{"key":"e_1_2_3_44_1","unstructured":"For limited examples on [3+n] (n\u22653) cycloaddition reactions of activated isocyanides in a non-catalytic enantioselective manner see:"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol501829k"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC08382B"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00986"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01948"},{"key":"e_1_2_3_49_1","unstructured":"\u00a0"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201402788"},{"key":"e_1_2_3_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201402788"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja511895q"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01851"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC03468G"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c01632"},{"key":"e_1_2_3_55_1","unstructured":"For selected reviews on azomethine imines see:"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201400631"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB01086A"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23010003"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1NJ01090E"},{"key":"e_1_2_3_60_1","unstructured":"For selected reviews on 1 2 4-triazines see:"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.08.009"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.11.027"},{"key":"e_1_2_3_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2021.113537"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00611"},{"key":"e_1_2_3_65_2","first-page":"409","volume":"37","author":"Fraser R. C.","year":"1987","journal-title":"J. Roy. Coll. Gen. Practit."},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.1158\/0008-5472.CAN-20-0782"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-019-56302-4"},{"key":"e_1_2_3_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b10939"},{"key":"e_1_2_3_69_1","unstructured":"Deposition Number2141843 (for5e\u20222DMSO)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_70_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00628G"},{"key":"e_1_2_3_72_2","doi-asserted-by":"publisher","DOI":"10.1080\/17460441.2019.1653850"},{"key":"e_1_2_3_73_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2020.07.007"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-021-00300-6"},{"key":"e_1_2_3_75_1","unstructured":"For limited examples on the kinetic resolution of racemic azomethine imines see:"},{"key":"e_1_2_3_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052876h"},{"key":"e_1_2_3_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja411110f"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507548"},{"key":"e_1_2_3_78_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507548"},{"key":"e_1_2_3_79_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms12720"},{"key":"e_1_2_3_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201600961"},{"key":"e_1_2_3_81_1","unstructured":"Deposition Number2132280 (for7\u2009a)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_82_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_3_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400215u"},{"key":"e_1_2_3_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00217"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.12.48"},{"key":"e_1_2_3_86_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA21191G"},{"key":"e_1_2_3_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00322"},{"key":"e_1_2_3_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00740"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202202679","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202202679","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202202679","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,24]],"date-time":"2023-08-24T13:33:08Z","timestamp":1692883988000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202202679"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,3,30]]},"references-count":99,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2022,6,7]]}},"alternative-id":["10.1002\/anie.202202679"],"URL":"https:\/\/doi.org\/10.1002\/anie.202202679","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,3,30]]},"assertion":[{"value":"2022-02-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-03-30","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202202679"}}