{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T21:25:55Z","timestamp":1790976355834,"version":"4.1.0"},"reference-count":22,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2025,5,8]],"date-time":"2025-05-08T00:00:00Z","timestamp":1746662400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004423","name":"Waseda University","doi-asserted-by":"publisher","award":["2024C\u2010161"],"award-info":[{"award-number":["2024C\u2010161"]}],"id":[{"id":"10.13039\/501100004423","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,6,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In this paper, we describe a chiral Rh\u2010catalyzed [2\u00a0+\u00a02\u00a0+\u00a02] cycloaddition of 1,8\u2010naphthylene\u2010based 1,10\u2010diynes of an <jats:italic>anti<\/jats:italic>\/<jats:italic>syn<\/jats:italic> mixture with alkynoates. Thermodynamically stable saddle\u2010shaped chiral cycloadducts were obtained in good\u2010to\u2010high yields and enantiomeric ratios. Hetero [2\u00a0+\u00a02\u00a0+\u00a02] cycloaddition using aryl cyanides also proceeded to give the corresponding inherently chiral pyridine\u2010containing compounds.<\/jats:p>","DOI":"10.1002\/chem.202501193","type":"journal-article","created":{"date-parts":[[2025,4,28]],"date-time":"2025-04-28T03:50:40Z","timestamp":1745812240000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Catalytic and Enantioselective Synthesis of Inherently Chiral Saddle\u2010Shaped Compounds by [2\u00a0+\u00a02\u00a0+\u00a02] Cycloaddition of 1,8\u2010Naphthylene\u2010Based 1,10\u2010Diynes with Alkynoates"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4436-8264","authenticated-orcid":false,"given":"Takanori","family":"Shibata","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University  3\u20104\u20101 Okubo Shinjuku Tokyo 169\u20138555 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masahiro","family":"Nakada","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University  3\u20104\u20101 Okubo Shinjuku Tokyo 169\u20138555 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kousuke","family":"Senda","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University  3\u20104\u20101 Okubo Shinjuku Tokyo 169\u20138555 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mamoru","family":"Ito","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University  3\u20104\u20101 Okubo Shinjuku Tokyo 169\u20138555 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,5,8]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202300738"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1093\/nsr\/nwx122"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2023.154429"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00241-1"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903715"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201511876"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201701532"},{"key":"e_1_2_8_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201900051"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.021.202101486"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.202400243"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.checat.2023.100827"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-52823-3"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202416873"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202319289"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1316793"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c02712"},{"key":"e_1_2_8_12_1","unstructured":"The formation of the dimer(s) and trimer(s) of diyne 1a was ascertained by mass spectrometric analysis because they could not be isolated."},{"key":"e_1_2_8_13_1","unstructured":"The reprecipitation of compound 3aa (er: 92:8) from dichloromethane a good solvent and hexane a poor solvent gave racemic crystals and the e.r. value of the mother solution was improved to about 95:5."},{"key":"e_1_2_8_14_1","unstructured":"CCDC2432991for 3aa contains the supplementary crystallographic data. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe (http:\/\/www.ccdc.cam.ac.uk\/structures)."},{"key":"e_1_2_8_15_1","unstructured":"We stopped the reaction for 5\u00a0min and ascertained that the e.r. of the recovered diyne anti\u20101a was 50:50."},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c18319"},{"key":"e_1_2_8_17_1","unstructured":"See supplementary materials in details."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202501193","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:45:33Z","timestamp":1760273133000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202501193"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,8]]},"references-count":22,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2025,6,6]]}},"alternative-id":["10.1002\/chem.202501193"],"URL":"https:\/\/doi.org\/10.1002\/chem.202501193","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,8]]},"assertion":[{"value":"2025-03-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-04-25","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202501193"}}