{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,30]],"date-time":"2026-10-30T02:05:30Z","timestamp":1793325930666,"version":"4.5.0"},"reference-count":22,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2022YFF0709803"],"award-info":[{"award-number":["2022YFF0709803"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007302","name":"Beijing University of Chemical Technology","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100007302","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Bicyclo[1.1.0]butanes (BCBs) have emerged as versatile strained building blocks for constructing stereodefined cyclic scaffolds. However, the Lewis-acid-catalyzed reaction of BCBs and ketones remains elusive, hampered by the poor electrophilicity and substantial steric hindrance of the ketonic carbonyl group. The La(OTf)3-catalyzed reaction of BCBs and isatins achieved highly stereoselective synthesis of 3-(cyclobuten-3-yl)-3-hydroxyindolin-2-ones in up to 97% yield with excellent diastereoselectivity (dr of &amp;gt;20:1). Control experiments and density functional theory calculations corroborate the reaction as a Baylis\u2013Hillman-type ring-opening activation strategy with isatin derivatives as representative cyclic ketones, revealing that the amidic carbonyl moiety of isatins stabilizes the key carbocation intermediates, which is the primary origin of the observed high diastereoselectivity. Notably, partial products precipitate spontaneously and can be isolated via simple filtration without tedious column chromatography, facilitating scale-up preparation. This protocol provides an efficient avenue to functionalized heterocyclic scaffolds and expands the synthetic utility of BCBs.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01677","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T21:02:16Z","timestamp":1790715736000},"page":"13694-13701","source":"Crossref","is-referenced-by-count":1,"title":["Highly Stereoselective\nReaction of Bicyclo[1.1.0]butanes\nand Isatins"],"prefix":"10.1021","volume":"91","author":[{"given":"Chengzhuo","family":"Wang","sequence":"first","affiliation":[{"name":"Beijing University of Chemical Technology , , ,","place":["Beijing, China, 100029"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weimeng","family":"Ma","sequence":"additional","affiliation":[{"name":"Beijing University of Chemical Technology , , ,","place":["Beijing, China, 100029"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9039-4933","authenticated-orcid":true,"given":"Jiaxi","family":"Xu","sequence":"additional","affiliation":[{"name":"Beijing University of Chemical Technology , , ,","place":["Beijing, China, 100029"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,29]]},"reference":[{"key":"2026101608084149500_cit1","doi-asserted-by":"publisher","first-page":"487","DOI":"10.1021\/ja00955a020","article-title":"Bicyclo[1.1.0]butane Chemistry. 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Sci."},{"key":"2026101608084149500_cit3a","doi-asserted-by":"publisher","first-page":"13060","DOI":"10.1039\/D3SC04457B","article-title":"Photochemical\n\u03b1-Selective Radical Ring-Opening Reactions of 1,3-Disubstituted\nAcyl Bicyclobutanes with Alkyl Halides: Modular Access to Functionalized\nCyclobutenes","volume":"14","author":"Xiao","year":"2023","journal-title":"Chem. Sci."},{"key":"2026101608084149500_cit3b","doi-asserted-by":"publisher","first-page":"7648","DOI":"10.1021\/jacs.1c03492","article-title":"Use of Strain-Release\nfor the Diastereoselective Construction of Quaternary Carbon Centers","volume":"143","author":"Pinkert","year":"2021","journal-title":"J. Am. Chem. 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Front."},{"key":"2026101608084149500_cit15","unstructured":"Ren, B.; Zhou, C.; Wang, H.\n          Substituted 5-(3,5-Dimethylisoxazol-4-yl)indolin-2-ones. WO Patent 2014173241 A1, Oct 30, 2014."},{"key":"2026101608084149500_cit16","doi-asserted-by":"publisher","first-page":"5121","DOI":"10.1021\/acs.jmedchem.6b00400","article-title":"Isatin Derived\nSpirocyclic Analogues with \u03b1-Methylene-\u03b3-Butyrolactone\nas Anticancer Agents: A Structure\u2013Activity Relationship Study","volume":"59","author":"Rana","year":"2016","journal-title":"J. Med. Chem."},{"key":"2026101608084149500_cit17","doi-asserted-by":"publisher","first-page":"1020","DOI":"10.1021\/ja067552n","article-title":"Synthesis\nand Cellular Profiling\nof Diverse Organosilicon Small Molecules","volume":"129","author":"Franz","year":"2007","journal-title":"J.\nAm. Chem. 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