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Adv."],"published-print":{"date-parts":[[2026,10,9]]},"abstract":"<jats:p>\n                    Isotopic chirality arising from hydrogen\/deuterium substitution has long resisted optical resolution because isotopic substitution introduces only minimal stereochemical differences, rendering such molecules structurally pseudo-achiral. Recognizing that the small yet distinct difference in C\u2013H\/C\u2013D bond dissociation energies (BDEs) creates an energetic asymmetry, we envisioned that an enantioselective C\u2013H functionalization exploiting this disparity could achieve the kinetic resolution of isotopically chiral molecules. Here, we report a catalytic method for the optical resolution of benzylic and allylic H\/D isotopic chirality. This method achieved a remarkably high separation factor (\n                    <jats:italic toggle=\"yes\">S<\/jats:italic>\n                    \u00a0=\u00a083.1), enabling the isolation of highly enantioenriched isotopically chiral substrates from racemic mixtures and revealing retention of stereochemical memory during radical recombination in asymmetric C\u2013H functionalization.\n                  <\/jats:p>","DOI":"10.1126\/sciadv.aed4187","type":"journal-article","created":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T17:58:33Z","timestamp":1791395913000},"update-policy":"https:\/\/doi.org\/10.34133\/aaas_crossmark","source":"Crossref","is-referenced-by-count":0,"title":["Optical resolution of H\/D isotopic chirality via asymmetric C\u2013H amination"],"prefix":"10.1126","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6511-5752","authenticated-orcid":true,"given":"Tatsuya","family":"Uchida","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Sciences, Kyushu University; Fukuoka, 819-0395, Japan."},{"name":"International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University; Fukuoka, 819-0395, Japan."},{"name":"Faculty of Arts and Science, Kyushu University; Fukuoka, 819-0395, Japan."},{"name":"JST PRESTO; Tokyo, 102-0076, Japan."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-3858-7007","authenticated-orcid":true,"given":"Yuta","family":"Nakagawa","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Sciences, Kyushu University; Fukuoka, 819-0395, Japan."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Naoki","family":"Watari","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Sciences, Kyushu University; Fukuoka, 819-0395, Japan."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3354-1690","authenticated-orcid":true,"given":"Yuuya","family":"Kawasaki","sequence":"additional","affiliation":[{"name":"Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580, Japan."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03219"},{"key":"e_1_3_2_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/D5SC09200K"},{"key":"e_1_3_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00007a009"},{"key":"e_1_3_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00100a033"},{"key":"e_1_3_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011685l"},{"key":"e_1_3_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol020038b"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00260A"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c00884"},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.3c00028"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23596"},{"key":"e_1_3_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202525850"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature05653"},{"key":"e_1_3_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp031284n"},{"key":"e_1_3_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00375a055"},{"key":"e_1_3_2_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/b908754k"},{"key":"e_1_3_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.201100155"},{"key":"e_1_3_2_18_2","doi-asserted-by":"crossref","unstructured":"D. Arigoni E. L. Eliel Chirality Due to the Presence of Hydrogen Isotopes at Noncyclic Positions. In Topics in Stereochemistry; N. L. Allinger E. L. Eliel Eds. (John Wiley & Sons Inc. New York 1969) vol. 4 pp 127\u2013243.","DOI":"10.1002\/9780470147139.ch4"},{"key":"e_1_3_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900121"},{"key":"e_1_3_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00225a067"},{"key":"e_1_3_2_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/JR9380001069"},{"key":"e_1_3_2_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/JR9360000808"},{"key":"e_1_3_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01272a072"},{"key":"e_1_3_2_24_2","article-title":"Optical resolution of C6D5CH(OH)C6D6 and C6H5CD(OH)C6H5 \u2013 Preparation and racemisation of (\u2212)-C6H5CHClC6D5 and (\u2212)-C6H5CDClC6D5","volume":"140","author":"Pocker Y.","year":"1961","unstructured":"Y. Pocker, Optical resolution of C6D5CH(OH)C6D6 and C6H5CD(OH)C6H5 \u2013 Preparation and racemisation of (\u2212)-C6H5CHClC6D5 and (\u2212)-C6H5CDClC6D5. Proc. Chem. Soc. 140\u2013141 (1961).","journal-title":"Proc. Chem. 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Kagan J. C. Fiaud New Approaches in Asymmetric Synthesis. Topics in Stereochemistry Eds. Eliel E. L. and Allinger N. L. John Wiley and Sons New York pp. 175\u2013285 (1979).","DOI":"10.1002\/9780470147191.ch3"},{"key":"e_1_3_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm300884k"},{"key":"e_1_3_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00393a045"}],"container-title":["Science Advances"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.science.org\/doi\/pdf\/10.1126\/sciadv.aed4187","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T17:59:32Z","timestamp":1791395972000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.science.org\/doi\/10.1126\/sciadv.aed4187"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,9]]},"references-count":37,"journal-issue":{"issue":"41","published-print":{"date-parts":[[2026,10,9]]}},"alternative-id":["10.1126\/sciadv.aed4187"],"URL":"https:\/\/doi.org\/10.1126\/sciadv.aed4187","relation":{},"ISSN":["2375-2548"],"issn-type":[{"value":"2375-2548","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,9]]},"assertion":[{"value":"2025-11-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-08-28","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-07","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"eaed4187"}}