{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,12]],"date-time":"2026-06-12T02:43:02Z","timestamp":1781232182966,"version":"3.54.1"},"reference-count":80,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2022,5,16]],"date-time":"2022-05-16T00:00:00Z","timestamp":1652659200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004051","name":"Kato Memorial Bioscience Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004051","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100011313","name":"Tokyo Biochemical Research Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100011313","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100008965","name":"Takahashi Industrial and Economic Research Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100008965","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2022,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>An unprecedented Ag\u2010catalyzed <jats:italic>exo\u2032<\/jats:italic>\u2010selective [3+2] cycloaddition of imino esters with 4\u2010benzylidene\u20102,3\u2010dioxopyrrolidines is described. The reaction was efficiently catalyzed by Ag\/(<jats:italic>R<\/jats:italic>, <jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)\u2010ThioClickFerrophos (TCF) leading to the construction of the corresponding spirobipyrrolidine scaffolds in excellent enantio\u2010 and diastereoselectivities. This reaction is the first example of a silver\u2010catalyzed <jats:italic>exo\u2032<\/jats:italic>\u2010selective asymmetric [3+2] cycloaddition, as well as the first <jats:italic>exo\u2032<\/jats:italic>\u2010selective spirobipyrrolidine construction via a [3+2] cycloaddition process using imino esters. The wide substrate scope of this reaction enabled the preparation of structurally diverse spirobipyrrolidine derivatives, which are attracting attention as targets for drug discovery. Mechanistic studies suggested that the unusual <jats:italic>exo\u2032<\/jats:italic>\u2010selectivity of this reaction is not due to epimerization following the common <jats:italic>exo<\/jats:italic>\u2010 or <jats:italic>endo<\/jats:italic>\u2010selective cycloaddition, but instead is due to a stepwise Michael addition\/Mannich sequence with bond rotation.<\/jats:p>","DOI":"10.1002\/asia.202200239","type":"journal-article","created":{"date-parts":[[2022,4,29]],"date-time":"2022-04-29T14:05:49Z","timestamp":1651241149000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["<i>exo\u2032<\/i>\u2010Selective Construction of Spirobipyrrolidines by the Silver\u2010catalyzed Asymmetric [3+2] Cycloaddition of Imino Esters with 4\u2010Benzylidene\u20102,3\u2010dioxopyrrolidines"],"prefix":"10.1002","volume":"17","author":[{"given":"Shohei","family":"Furuya","sequence":"first","affiliation":[{"name":"Faculty of Science and Engineering Chuo University  1-13-27 Kasuga Bunkyo-ku 112-8551 Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3958-7369","authenticated-orcid":false,"given":"Kazuya","family":"Kanemoto","sequence":"additional","affiliation":[{"name":"Faculty of Science and Engineering Chuo University  1-13-27 Kasuga Bunkyo-ku 112-8551 Tokyo Japan"},{"name":"Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku 980-8578 Sendai Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8108-3829","authenticated-orcid":false,"given":"Shin\u2010ichi","family":"Fukuzawa","sequence":"additional","affiliation":[{"name":"Faculty of Science and Engineering Chuo University  1-13-27 Kasuga Bunkyo-ku 112-8551 Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,5,16]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(96)00737-5"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.49.832"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np980410p"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja051147z"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm051122a"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0708917105"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802179e"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201109221"},{"key":"e_1_2_8_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201109221"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4025937"},{"key":"e_1_2_8_11_1","unstructured":"\u00a0"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200907108"},{"key":"e_1_2_8_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200907108"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500127b"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c01473"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702362"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201703801"},{"key":"e_1_2_8_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201703801"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03502"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b00896"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC03676E"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1RA00841B"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02686B"},{"key":"e_1_2_8_23_1","unstructured":"\u00a0"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00943a"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100104"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201201249"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc40669e"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc45493b"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201410782"},{"key":"e_1_2_8_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201410782"},{"key":"e_1_2_8_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC02362A"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02387"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00734"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202108072"},{"key":"e_1_2_8_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202108072"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC05238K"},{"key":"e_1_2_8_35_1","unstructured":"\u00a0"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004098"},{"key":"e_1_2_8_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004098"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc43025a"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405223"},{"key":"e_1_2_8_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201405223"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB02278A"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b01743"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.02.099"},{"key":"e_1_2_8_42_1","unstructured":"\u00a0"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201908227"},{"key":"e_1_2_8_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201908227"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00509"},{"key":"e_1_2_8_45_1","unstructured":"For selected examples using trifluoromethylated azomethine ylides:"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00723F"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00283"},{"key":"e_1_2_8_48_1","unstructured":"\u00a0"},{"key":"e_1_2_8_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.08.002"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201706033"},{"key":"e_1_2_8_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c01440"},{"key":"e_1_2_8_52_1","unstructured":"\u00a0"},{"key":"e_1_2_8_53_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.03.024"},{"key":"e_1_2_8_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02024"},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2017.02.001"},{"key":"e_1_2_8_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b01335"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02309"},{"key":"e_1_2_8_58_1","unstructured":"\u00a0"},{"key":"e_1_2_8_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9QO00452A"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202000001"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202000073"},{"key":"e_1_2_8_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB01223A"},{"key":"e_1_2_8_63_1","unstructured":"\u00a0"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00961"},{"key":"e_1_2_8_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC05001H"},{"key":"e_1_2_8_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711813"},{"key":"e_1_2_8_66_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711813"},{"key":"e_1_2_8_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b00839"},{"key":"e_1_2_8_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB00419J"},{"key":"e_1_2_8_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201900254"},{"key":"e_1_2_8_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c00976"},{"key":"e_1_2_8_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC00707F"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202200239","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/asia.202200239","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202200239","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T14:49:35Z","timestamp":1759934975000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.202200239"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,16]]},"references-count":80,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2022,8]]}},"alternative-id":["10.1002\/asia.202200239"],"URL":"https:\/\/doi.org\/10.1002\/asia.202200239","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,5,16]]},"assertion":[{"value":"2022-03-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-05-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200239"}}