{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T15:55:19Z","timestamp":1792598119091,"version":"4.5.0"},"reference-count":31,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T00:00:00Z","timestamp":1791417600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T00:00:00Z","timestamp":1791417600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T00:00:00Z","timestamp":1791417600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100004921","name":"Shanghai Jiao Tong University","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004921","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100009002","name":"Shanghai University","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100009002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22371183"],"award-info":[{"award-number":["22371183"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22501166"],"award-info":[{"award-number":["22501166"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,21]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The Berson\u2013Willcott rearrangement (BWR) has long been restricted to all-carbon systems, hampered by harsh conditions, reversible equilibria, and underexplored stereochemistry. Herein, we disclose the first aza-Berson\u2013Willcott rearrangement transformation. By circumventing the all-carbon constraint, this strategy enables the efficient construction of cyclopropane-fused quinolines with complete regio- and diastereocontrol under operationally simple conditions. Density functional theory calculations unravel a distinctive noncanonical mechanistic pathway, wherein ring expansion toward a benzazepine intermediate, conformational inversion, and successive ring closure collectively govern the high-fidelity stereospecificity of this transformation. This method directly converts planar quinolines and analogues into rigid three-dimensional bicyclic scaffolds and enables late-stage cyclopropanation of pharmaceutically relevant agents. This work establishes a robust paradigm for precise stereochemical elaboration of heteroaromatic scaffolds and expands the chemical space accessible through sigmatropic rearrangements.<\/jats:p>","DOI":"10.1021\/jacs.6c17393","type":"journal-article","created":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T15:01:49Z","timestamp":1791471709000},"page":"45159-45166","source":"Crossref","is-referenced-by-count":0,"title":["Aza-Berson\u2013Willcott\nRearrangement"],"prefix":"10.1021","volume":"148","author":[{"given":"Yu-Ping","family":"He","sequence":"first","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]},{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ping","family":"Pu","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]},{"name":"Shanghai University , , ,","place":["Shanghai, China, 200444"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fang-Zhou","family":"Li","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng","family":"Yuan","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lu-Sen","family":"Yang","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0401-2434","authenticated-orcid":true,"given":"Hua","family":"Wu","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,8]]},"reference":[{"key":"2026102111081642900_cit1","doi-asserted-by":"publisher","first-page":"2494","DOI":"10.1021\/ja00963a025","article-title":"Berson-Willcott Rearrangement: Stereospecific Thermal\nRearrangement of Cyclopropanaphthalene Derivatives","volume":"88","author":"Berson","year":"1966","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111081642900_cit2","doi-asserted-by":"publisher","first-page":"152","DOI":"10.1021\/ar50005a004","article-title":"The stereochemistry\nof sigmatropic rearrangements. Tests of the predictive power of orbital\nsymmetry rules","volume":"1","author":"Berson","year":"1968","journal-title":"Acc. Chem. Res."},{"key":"2026102111081642900_cit3","doi-asserted-by":"publisher","first-page":"2857","DOI":"10.1021\/ja00374a027","article-title":"Stereochemistry of the Thermal Rearrangements of Methyl-Substituted\nCycloheptatrienes","volume":"104","author":"Baldwin","year":"1982","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111081642900_cit4","doi-asserted-by":"publisher","first-page":"4524","DOI":"10.1021\/ja9840192","article-title":"Origin\nof the Preference\nfor the Orbital Symmetry Forbidden Stereochemistry of the 1,5-Sigmatropic\nShift of Substituted Norcaradienes","volume":"121","author":"Kless","year":"1999","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026102111081642900_cit5","doi-asserted-by":"publisher","first-page":"402","DOI":"10.1002\/anie.196704021","article-title":"The Norcaradiene\nProblem","volume":"6","author":"Maier","year":"1967","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"2026102111081642900_cit6","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1016\/j.tet.2010.10.030","article-title":"The norcaradiene\u2013cycloheptatriene\nequilibrium","volume":"67","author":"McNamara","year":"2011","journal-title":"Tetrahedron"},{"key":"2026102111081642900_cit7","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415839","article-title":"Catalytic Dearomative [1,5]-Sigmatropic\nCarbon Shift of Heterole-Fused Norcaradienes Enabled Concise Helicenation","volume":"64","author":"Bi","year":"2025","journal-title":"Angew. Chem., Int. 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Compd."},{"key":"2026102111081642900_cit18","doi-asserted-by":"publisher","first-page":"534","DOI":"10.1021\/jo01133a010","article-title":"Recent Japanese\nwork on the chemistry of pyridine 1-oxide and related compounds","volume":"18","author":"Ochiai","year":"1953","journal-title":"J. Org. Chem."},{"key":"2026102111081642900_cit19","doi-asserted-by":"publisher","first-page":"1545","DOI":"10.3987\/r-1983-08-1545","article-title":"The reaction of 2-substituted\nquinoline 1-oxides with\ndimethyl acetylenedicarboxylate: formation of 1-benzazepine derivatives","volume":"20","author":"Hamana","year":"1983","journal-title":"Heterocycles"},{"key":"2026102111081642900_cit20","doi-asserted-by":"publisher","first-page":"952","DOI":"10.1038\/s41557-025-01793-0","article-title":"Switchable skeletal\nediting of quinolines enabled by cyclizative sequential rearrangements","volume":"17","author":"Tian","year":"2025","journal-title":"Nat. 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