{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T01:40:09Z","timestamp":1777426809852,"version":"3.51.4"},"reference-count":68,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2026,4,20]],"date-time":"2026-04-20T00:00:00Z","timestamp":1776643200000},"content-version":"vor","delay-in-days":19,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"},{"start":{"date-parts":[[2026,4,1]],"date-time":"2026-04-01T00:00:00Z","timestamp":1775001600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100007656","name":"Iwatani Naoji Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100007656","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010981","name":"Izumi Science and Technology Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100010981","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2026,4]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Resorcinarene\u2010based coordination capsules provide rigid, well\u2010defined cavities that can exhibit helicity under chiral induction, a feature that has previously been exploited using axially chiral biphenyl compounds and tartaric acid derivatives. However, these approaches generally require well\u2010designed templates tailored to the capsule structures. In this study, it was discovered that commercially available mandelic acid functions as an effective and operationally simple additive for inducing chirality in an empty\u2010cavity Cu(I) capsule without the requirement for templates. Chiral induction was achieved by introducing mandelic acid through either treatment of a preformed racemic capsule or during its assembly. Both approaches generated helically biased capsules, as confirmed by circular dichroism and nuclear magnetic resonance (NMR) spectroscopy, with optical purities approaching unity (up to \u223c97% ee) under optimized conditions. Mechanistic investigations using NMR spectroscopy, electrospray ionization mass spectrometry, and electron spin resonance spectroscopy indicated that the oxidation of Cu(I) to Cu(II) played a key role in the induction process, and that this was mediated by interactions with the carboxylate group of mandelic acid. This study therefore presents a straightforward and highly effective protocol for accessing an enantiomerically enriched resorcinarene\u2010based coordination capsule, expanding its potential as a confined chiral reaction space and a functional chiral material.<\/jats:p>","DOI":"10.1002\/asia.70748","type":"journal-article","created":{"date-parts":[[2026,4,20]],"date-time":"2026-04-20T07:24:02Z","timestamp":1776669842000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Mandelic Acid\u2010Mediated Enantiomeric Enrichment of a Resorcinarene\u2010Based Dissymmetric Coordination Capsule"],"prefix":"10.1002","volume":"21","author":[{"given":"Senri","family":"Miyagi","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University 1\u20103\u20101 Kagamiyama Higashi\u2010Hiroshima Hiroshima Japan"},{"name":"International Institute for Sustainability with Knotted Chiral Meta Matter (WPI\u2010SKCM\u00b2) Hiroshima University 1\u20103\u20101 Kagamiyama Higashi\u2010Hiroshima Hiroshima Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-0694-7321","authenticated-orcid":false,"given":"Yudai","family":"Ono","sequence":"additional","affiliation":[{"name":"International Institute for Sustainability with Knotted Chiral Meta Matter (WPI\u2010SKCM\u00b2) Hiroshima University 1\u20103\u20101 Kagamiyama Higashi\u2010Hiroshima Hiroshima Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2013-4394","authenticated-orcid":false,"given":"Manabu","family":"Abe","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University 1\u20103\u20101 Kagamiyama Higashi\u2010Hiroshima Hiroshima 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capsule possesses four equivalent portals.Encapsulation ofG2can generate three conformational isomers defined by the dihedral angle of the biphenyl ester units. In asyn\u2010periplanar arrangement the two benzyl arms occupy a single portal. In a clinal conformation (dihedral angle \u2248 90\u00b0) they extend toward two adjacent portals. In ananti\u2010periplanar conformation the benzyl arms project toward two opposite portals. The three acetyl signals observed at \u22121.4\u00a0ppm are tentatively attributed to these conformational isomers of the host\u2013guest complex."},{"key":"e_1_2_7_63_1","unstructured":"Tetrabutyl mandelate instead of mandelic acid and was examined for the one\u2010pot process The enantiomeric enrichment yielded aneeof 50% Which is somewhat lower than that observed with mandelic acid the Cu(I)\/Cu(II) interconversion requires acidic conditions (Figure S9) as shown in Scheme 2."},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00636"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00297"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229624007617"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00834-8"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC00570K"},{"key":"e_1_2_7_69_1","unstructured":"M. J.Frisch G. W.Trucks H. B.Schlegel et al. Gaussian 16 Revision C. 02 Gaussian Inc. Wallingford CT (2019)."}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.70748","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/asia.70748","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.70748","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,28]],"date-time":"2026-04-28T11:32:42Z","timestamp":1777375962000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.70748"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,4]]},"references-count":68,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2026,4]]}},"alternative-id":["10.1002\/asia.70748"],"URL":"https:\/\/doi.org\/10.1002\/asia.70748","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,4]]},"assertion":[{"value":"2025-10-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-04-08","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-04-20","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70748"}}