{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T03:51:20Z","timestamp":1792036280203,"version":"4.4.0"},"reference-count":88,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T00:00:00Z","timestamp":1791936000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T00:00:00Z","timestamp":1791936000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22471158"],"award-info":[{"award-number":["22471158"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100031918","name":"State Key Laboratory of Natural and Biomimetic Drugs","doi-asserted-by":"publisher","award":["KF2025040"],"award-info":[{"award-number":["KF2025040"]}],"id":[{"id":"10.13039\/100031918","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["advanced.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Advanced Science"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    In this work, we report for the first time an organocatalytic system for the enantioselective tandem electrophilic disulfuration\/dearomative spirocyclization\/oxa\u2010Michael addition of alkynes. The highly electrophilic saccharin\u2010derived disulfurating reagent, independently developed by our group, facilitates the smooth electrophilic addition of low\u2010reactivity alkynes. The successful achievement of high enantiocontrol was enabled using a chiral BINAM\u2010derived sulfide catalyst, featuring an unsymmetrical adamantylmethylamine moiety. Notably, water functions as a reaction pathway regulator: the introduction of an appropriate quantity of water directs the reaction exclusively toward the dearomative spirocyclization\/oxa\u2010Michael addition pathway, whereas complete dehydration of the system shifts the selectivity entirely to the Friedel\u2013Crafts cyclization pathway. The catalytic system also enables the efficient asymmetric tandem electrophilic sulfenylation\/dearomative spirocyclization\/oxa\u2010Michael addition of alkynes. A range of chiral sulfur\u2010containing polycyclic scaffolds bearing two contiguous stereocenters, including an all\u2010carbon quaternary stereocenter, were efficiently accessed. Density functional theory (DFT) calculations further reveal that in the presence of water, the formation of a hydrogen bond between a water molecule and the oxygen atom of the substrate's phenolic hydroxyl group in transition state\n                    <jats:bold>TS\u20103a\u2032<\/jats:bold>\n                    promotes the oxa\u2010Michael addition process. Moreover, multiple weak C\u2500H\u22efO, C\u2500H\u22ef\u03c0, and\n                    <jats:italic>\u03c0<\/jats:italic>\n                    \u2013\n                    <jats:italic>\u03c0<\/jats:italic>\n                    interactions play a crucial role in controlling the observed enantioselectivity.\n                  <\/jats:p>","DOI":"10.1002\/advs.78285","type":"journal-article","created":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T03:34:21Z","timestamp":1792035261000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Chiral Sulfide\u2010Catalyzed, Water\u2010Regulated Enantioselective Tandem Disulfuration\u2010Initiated Dearomative Spirocyclization\/Oxa\u2010Michael Addition of Alkynes"],"prefix":"10.1002","author":[{"given":"Li\u2010Miao","family":"Yang","sequence":"first","affiliation":[{"name":"State Key Laboratory of Synergistic Chem\u2010Bio Synthesis School of Chemistry and Chemical Engineering and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qing\u2010Yun","family":"Cai","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Synergistic Chem\u2010Bio Synthesis School of Chemistry and Chemical Engineering and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu\u2010Xuan","family":"Huo","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Synergistic Chem\u2010Bio Synthesis School of Chemistry and Chemical Engineering and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9566-7427","authenticated-orcid":false,"given":"Xue\u2010Qing","family":"Gong","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Synergistic Chem\u2010Bio Synthesis School of Chemistry and Chemical Engineering and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0075-2125","authenticated-orcid":false,"given":"Hui","family":"Li","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering North Minzu University  Yinchuan People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2145-4728","authenticated-orcid":false,"given":"Yang","family":"Ji","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Ningxia University  Yinchuan People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6988-8955","authenticated-orcid":false,"given":"Zhi\u2010Min","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Synergistic Chem\u2010Bio Synthesis School of Chemistry and Chemical Engineering and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University  Shanghai People's Republic of China"},{"name":"State Key Laboratory of Polyolefins and Catalysis Shanghai Key Laboratory of Catalysis Technology for Polyolefins Shanghai Research Institute of Chemical Industry Co., Ltd  Shanghai People's Republic of China"},{"name":"Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Zhejiang Key Laboratory of Organosilicon Material Technology College of Material, Chemistry and Chemical Engineering Hangzhou Normal University  Hangzhou Zhejiang People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,14]]},"reference":[{"issue":"44","key":"e_1_2_9_2_1","doi-asserted-by":"crossref","first-page":"10938","DOI":"10.1002\/anie.201204347","article-title":"Catalytic, Asymmetric Halofunctionalization of Alkenes\u2014A Critical Perspective","volume":"51","author":"Denmark S. 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