{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T11:27:45Z","timestamp":1792668465309,"version":"4.5.0"},"reference-count":105,"publisher":"Wiley","issue":"29","license":[{"start":{"date-parts":[[2024,6,17]],"date-time":"2024-06-17T00:00:00Z","timestamp":1718582400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["020514380295"],"award-info":[{"award-number":["020514380295"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22273035"],"award-info":[{"award-number":["22273035"]}],"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":[[2024,7,15]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The exploration of the complex chemical diversity of bicyclo[n.1.1]alkanes and their use as benzene bioisosteres has garnered significant attention over the past two decades. Regiodivergent syntheses of thiabicyclo[4.1.1]octanes (S\u2010BCOs) and highly substituted bicyclo[2.1.1]hexanes (BCHs) using a Lewis acid\u2010catalyzed formal cycloaddition of bicyclobutanes (BCBs) and 3\u2010benzylideneindoline\u20102\u2010thione derivatives have been established. The first hetero\u2010(4+3) cycloaddition of BCBs, catalyzed by Zn(OTf)\n                    <jats:sub>2<\/jats:sub>\n                    , was achieved with a broad substrate scope under mild conditions. In contrast, the less electrophilic BCB ester undergoes a Sc(OTf)\n                    <jats:sub>3<\/jats:sub>\n                    \u2010catalyzed [2\u03c0+2\u03c3] reaction with 1,1,2\u2010trisubstituted alkenes, yielding BCHs with a spirocyclic quaternary carbon center. Control experiments and preliminary theoretical calculations suggest that the diastereoselective [2\u03c0+2\u03c3] product formation may involve a concerted cycloaddition between a zwitterionic intermediate and\n                    <jats:italic>E<\/jats:italic>\n                    \u20101,1,2\u2010trisubstituted alkenes. Additionally, the hetero\u2010(4+3) cycloaddition may involve a concerted nucleophilic ring\u2010opening mechanism.\n                  <\/jats:p>","DOI":"10.1002\/anie.202405222","type":"journal-article","created":{"date-parts":[[2024,5,10]],"date-time":"2024-05-10T22:08:26Z","timestamp":1715378906000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":119,"title":["Switching between the [2\u03c0+2\u03c3] and Hetero\u2010[4\u03c0+2\u03c3] Cycloaddition Reactivity of Bicyclobutanes with Lewis Acid Catalysts Enables the Synthesis of Spirocycles and Bridged Heterocycles"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0009-0007-8091-9728","authenticated-orcid":false,"given":"Ji\u2010Jie","family":"Wang","sequence":"first","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering Hunan University  Changsha, Hunan 410082 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1273-9040","authenticated-orcid":false,"given":"Lei","family":"Tang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering Hunan University  Changsha, Hunan 410082 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5155-9099","authenticated-orcid":false,"given":"Yuanjiu","family":"Xiao","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering Hunan University  Changsha, Hunan 410082 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-6598-2058","authenticated-orcid":false,"given":"Wen\u2010Biao","family":"Wu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering Hunan University  Changsha, Hunan 410082 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9666-1919","authenticated-orcid":false,"given":"Guoqiang","family":"Wang","sequence":"additional","affiliation":[{"name":"Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering Nanjing University  Nanjing 210093 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6094-3268","authenticated-orcid":false,"given":"Jian\u2010Jun","family":"Feng","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo\/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering Hunan University  Changsha, Hunan 410082 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,6,17]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00771"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-023-1533-y"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2023.10.002"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00125B"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508818"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300626"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.287.5460.1964"},{"key":"e_1_2_3_9_1","unstructured":"\u00a0"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00220A"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0QO01085E"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b03694"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02686B"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00508C"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC02364F"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs401172r"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300135y"},{"key":"e_1_2_3_18_1","unstructured":"\u00a0"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.06.056"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-015-9629-8"},{"key":"e_1_2_3_21_1","unstructured":"\u00a0"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm901241e"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2md20347b"},{"key":"e_1_2_3_24_1","unstructured":"\u00a0"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-0503-7"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c11563"},{"key":"e_1_2_3_27_1","unstructured":"For reviews on BCBs see:"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-022-00811-3"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC03948F"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1515\/pac-2019-1007"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC01771J"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500437h"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202400045"},{"key":"e_1_2_3_34_1","unstructured":"\u00a0"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00955a021"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)87348-8"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600723"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-04636-x"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c02976"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03222"},{"key":"e_1_2_3_41_2","first-page":"24466","volume":"145","author":"Robichon M.","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01135-y"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c00421"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202214507"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c00305"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.26434\/chemrxiv-2024-r9c2g"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.26434\/chemrxiv-2024-t9dqq"},{"key":"e_1_2_3_48_1","author":"Radhoff N.","year":"2023","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_3_49_1","unstructured":"\u00a0"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202204719"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC04234K"},{"key":"e_1_2_3_52_1","unstructured":"\u00a0"},{"key":"e_1_2_3_53_2","author":"Liang Y.","year":"2023","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09248"},{"key":"e_1_2_3_55_1","unstructured":"\u00a0"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c02961"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c12894"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202308606"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202310066"},{"key":"e_1_2_3_60_1","unstructured":"\u00a0"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c04071"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2QO00167E"},{"key":"e_1_2_3_63_1","unstructured":"\u00a0"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202004183"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c03606"},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC03083K"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02812E"},{"key":"e_1_2_3_68_1","unstructured":"\u00a0"},{"key":"e_1_2_3_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c10541"},{"key":"e_1_2_3_70_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-022-05290-z"},{"key":"e_1_2_3_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09733"},{"key":"e_1_2_3_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c11501"},{"key":"e_1_2_3_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c09789"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c13740"},{"key":"e_1_2_3_75_1","author":"Semeno V. V.","year":"2023","journal-title":"Chem. Eur. J."},{"key":"e_1_2_3_76_1","unstructured":"\u00a0"},{"key":"e_1_2_3_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00221a003"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201800167"},{"key":"e_1_2_3_79_1","unstructured":"\u00a0"},{"key":"e_1_2_3_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00443a002"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00336a038"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050104k"},{"key":"e_1_2_3_83_1","unstructured":"\u00a0"},{"key":"e_1_2_3_84_2","author":"Zhang J.","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_3_85_2","author":"Liang Y.","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_3_86_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adh9737"},{"key":"e_1_2_3_87_1","unstructured":"For recent reviews of [4+3] cycloaddition reactions see:"},{"key":"e_1_2_3_88_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-022-1471-2"},{"key":"e_1_2_3_89_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00532J"},{"key":"e_1_2_3_90_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc03620j"},{"key":"e_1_2_3_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202305450"},{"key":"e_1_2_3_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209266"},{"key":"e_1_2_3_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b04429"},{"key":"e_1_2_3_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201609608"},{"key":"e_1_2_3_95_1","unstructured":"\u00a0"},{"key":"e_1_2_3_96_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19930001835"},{"key":"e_1_2_3_97_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF03246223"},{"key":"e_1_2_3_98_1","unstructured":"\u00a0"},{"key":"e_1_2_3_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00549"},{"key":"e_1_2_3_100_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202100714"},{"key":"e_1_2_3_101_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111691"},{"key":"e_1_2_3_102_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.04.003"},{"key":"e_1_2_3_103_1","unstructured":"Deposition numbers 2339679 (for3\u2009ba) and 2339680 (for4\u2009ar) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structuresservice."},{"key":"e_1_2_3_104_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905539"},{"key":"e_1_2_3_105_1","first-page":"9","volume":"4","author":"Alonso R.","year":"2019","journal-title":"Core Evidence"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202405222","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,16]],"date-time":"2025-01-16T11:17:39Z","timestamp":1737026259000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202405222"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,17]]},"references-count":105,"journal-issue":{"issue":"29","published-print":{"date-parts":[[2024,7,15]]}},"alternative-id":["10.1002\/anie.202405222"],"URL":"https:\/\/doi.org\/10.1002\/anie.202405222","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,17]]},"assertion":[{"value":"2024-03-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-06-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202405222"}}