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Adv."],"published-print":{"date-parts":[[2026,7,17]]},"abstract":"<jats:p>\n                    The pursuit of high enantioselectivity remains a central challenge in the burgeoning area of radical\n                    <jats:italic toggle=\"yes\">N<\/jats:italic>\n                    -heterocyclic carbene (NHC) catalysis. Moreover, direct functionalizations of unstrained and unpolarized C\u2500C bonds continue to pose a formidable obstacle in organocatalysis. Herein, we disclose an asymmetric NHC organocatalytic platform that achieves highly enantioselective radical acylation of inert C(sp\n                    <jats:sup>2<\/jats:sup>\n                    )\u2500C(sp\n                    <jats:sup>3<\/jats:sup>\n                    ) bonds. Central to this advance is the development of a previously unknown collection of chiral thiazolium catalysts integrating medium-ring backbones with\n                    <jats:italic toggle=\"yes\">C<\/jats:italic>\n                    <jats:sub>2<\/jats:sub>\n                    -symmetric chiral units, which facilitate the stereoselective acylation of C\u2500C bonds through a Smiles-type rearrangement. This organocatalytic protocol affords more than 70 examples with outstanding yields (up to 99%) and excellent regioselectivity (up to 99:1 rr) and enantioselectivity (up to 99.5:0.5 er) under transition metal\u2013free and light-free conditions. The practicality of this strategy is further underscored by stereo-controlled late-stage functionalization of complex bioactive molecules. Mechanistic insights from combined experimental and computational studies support a radical-mediated catalytic cycle and elucidate the origin of enantioselectivity.\n                  <\/jats:p>","DOI":"10.1126\/sciadv.aeg0999","type":"journal-article","created":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T17:58:48Z","timestamp":1784311128000},"update-policy":"https:\/\/doi.org\/10.34133\/aaas_crossmark","source":"Crossref","is-referenced-by-count":1,"title":["Asymmetric radical NHC organocatalysis\u2013enabled highly enantioselective acylation of inert C(sp\n                    <sup>2<\/sup>\n                    )\u2500C(sp\n                    <sup>3<\/sup>\n                    ) bonds"],"prefix":"10.1126","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2041-6025","authenticated-orcid":true,"given":"Qing-Zhu","family":"Li","sequence":"first","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mei-Hao","family":"He","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."},{"name":"Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng-Tao","family":"Wang","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Long-Hai","family":"Hong","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ting","family":"Qi","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin-Xin","family":"Kou","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dong-Yang","family":"Xiang","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wan-Cong","family":"Liu","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zi-Jie","family":"Xing","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-2273-4981","authenticated-orcid":true,"given":"Xiang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4700-0142","authenticated-orcid":true,"given":"Jun-Long","family":"Li","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"crossref","unstructured":"P. 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