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Here we disclose a concise strategy that delivers pyrrolidine\u2010, piperidine\u2010, and azepane\u2010based tricyclic \u03b2\u2010lactams. A pyrimidinediimine\u2010iron catalyst first constructs the cyclobutane ring and the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocycle in one step through an intermolecular [2\u00a0+\u00a02]\u2010cycloaddition of allyl amines; a subsequent photochemical intramolecular C\u2500H insertion then forges the \u03b2\u2010lactam. The major products adopt rigid, cage\u2010like conformations confirmed for the pyrrolidine series by single\u2010crystal X\u2010ray diffraction. Comprehensive conformer sampling (using CREST), DFT\u2010calculated NMR shifts, and DP4 statistical analysis establish the stereochemistry across the library. Strain\u2010release opening of the \u03b2\u2010lactam ring furnishes methylphenidate analogues in a single step, underscoring the scaffolds\u2019 synthetic versatility. Comparative studies on the corresponding bicyclic systems highlight the unique three\u2010dimensionality imparted by the additional cyclobutane ring, further expanding the toolbox for lead\u2010oriented synthesis.\n                  <\/jats:p>","DOI":"10.1002\/chem.202502476","type":"journal-article","created":{"date-parts":[[2025,9,27]],"date-time":"2025-09-27T06:17:21Z","timestamp":1758953841000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of Cyclobutane\u2010Containing Tricyclic \u03b2\u2010Lactams Based on a Saturated Scaffold Enabled by Iron\u2010catalysed [2\u00a0+\u00a02]\u2010Cycloaddition"],"prefix":"10.1002","volume":"31","author":[{"given":"Lea","family":"Freitag","sequence":"first","affiliation":[{"name":"Anorganisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"},{"name":"Institut des Sciences Chimiques de Rennes Universit\u00e9 de Rennes  Rennes F\u201035000 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johannes","family":"Zeh","sequence":"additional","affiliation":[{"name":"Anorganisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Levi A.","family":"Ziegenhagen","sequence":"additional","affiliation":[{"name":"Anorganisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felix J.","family":"Becker","sequence":"additional","affiliation":[{"name":"Anorganisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0273-5495","authenticated-orcid":false,"given":"Drago\u0219\u2010Adrian","family":"Ro\u0219ca","sequence":"additional","affiliation":[{"name":"Anorganisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"},{"name":"Institut des Sciences Chimiques de Rennes Universit\u00e9 de Rennes  Rennes F\u201035000 France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,9,26]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1001\/jama.2018.19283"},{"key":"e_1_2_8_2_1","volume":"6","author":"Bush K.","year":"2016","journal-title":"Perspect. 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