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Herein, we introduce a new approach that utilizes a Lewis acid (Sc(OTf)\n                    <jats:sub>3<\/jats:sub>\n                    )\u2010catalyzed \u03c3\u2010bond cross\u2010exchange reaction between the C\u2212C bond of bicyclobutanes and the C\u2212N bond of diaziridines to produce multifunctionalized and medicinally interesting azabicyclo[3.1.1]heptane derivatives. The reaction proceeds well with different bicyclobutanes and a broad range of aryl\u2010 as well as alkenyl\u2010, but also alkyl\u2010substituted diaziridines (up to 98\u2009% yield). Conducting a scale\u2010up experiment and exploring the synthetic transformations of the cycloadducts emphasized the practical application of the synthesis. Furthermore, a zinc\u2010based chiral Lewis acid catalytic system was developed for the enantioselective version of this reaction (up to 96\u2009%\u2005\n                    <jats:italic>ee<\/jats:italic>\n                    ).\n                  <\/jats:p>","DOI":"10.1002\/anie.202416741","type":"journal-article","created":{"date-parts":[[2024,11,13]],"date-time":"2024-11-13T06:59:55Z","timestamp":1731481195000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":59,"title":["Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C\u2212C\/C\u2212N Bond Cross\u2010Exchange Reaction between Bicyclobutanes and Diaziridines"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-4575-148X","authenticated-orcid":false,"given":"Heng\u2010Xian","family":"He","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  410082 Changsha Hunan P.\u2005R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1918-1596","authenticated-orcid":false,"given":"Feng","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  410082 Changsha Hunan P.\u2005R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0799-5816","authenticated-orcid":false,"given":"Xu","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Chemistry &amp; Chemical Engineering Yangzhou University  225002 Yangzhou P.\u2005R. 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China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,22]]},"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":"10.1021\/acs.jmedchem.4c01122"},{"key":"e_1_2_3_4_1","unstructured":"For selected reviews 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