{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,2]],"date-time":"2026-05-02T13:02:28Z","timestamp":1777726948297,"version":"3.51.4"},"reference-count":50,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2023,2,10]],"date-time":"2023-02-10T00:00:00Z","timestamp":1675987200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000646","name":"Japan Society for the Promotion of Science London","doi-asserted-by":"publisher","award":["20H03364"],"award-info":[{"award-number":["20H03364"]}],"id":[{"id":"10.13039\/501100000646","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000646","name":"Japan Society for the Promotion of Science London","doi-asserted-by":"publisher","award":["20J20751"],"award-info":[{"award-number":["20J20751"]}],"id":[{"id":"10.13039\/501100000646","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":[[2023,3,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Asymmetric catalytic transformations of <jats:italic>N<\/jats:italic>\u2010unprotected cyclic carboxyimides such as succinimides, hydantoins, oxazolidinediones, and glitazones, is a powerful way of directly accessing variety of biologically valuable chiral compounds. Herein, a bis(trichlorosilyl) nucleophilic intermediate formed from cyclic carboxyimides was reacted with aldehydes via (<jats:italic>S<\/jats:italic>)\u2010SEGPHOS dioxide (SEGPHOSO), proceeding the aldol reaction in highly enantioselective fashion through a cyclic transition state. Furthermore, <jats:italic>N<\/jats:italic>\u2010unprotected carboxyimides were chemoselectively activated, even in the presence of <jats:italic>N<\/jats:italic>\u2010alkylated carboxyimides, to undergo stereoselective and chemoselective aldol reactions via <jats:italic>in\u2005situ<\/jats:italic> silicon tetrachloride activation. The functionalized cyclic carboxyimides is readily derived to the several synthetic units derivatization to various chiral building blocks without unnecessary protection\/deprotection steps.<\/jats:p>","DOI":"10.1002\/chem.202203506","type":"journal-article","created":{"date-parts":[[2022,12,16]],"date-time":"2022-12-16T23:06:20Z","timestamp":1671231980000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Enantioselective and Chemoselective Phosphine Oxide\u2010catalyzed Aldol Reactions of <i>N<\/i>\u2010Unprotected Cyclic Carboxyimides"],"prefix":"10.1002","volume":"29","author":[{"given":"Yusaku","family":"Yoshiwara","sequence":"first","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Kumamoto University  5-1 Oe-honmachi, Chuo-ku Kumamoto 862-0973 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4801-8341","authenticated-orcid":false,"given":"Shunsuke","family":"Kotani","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Kumamoto University  5-1 Oe-honmachi, Chuo-ku Kumamoto 862-0973 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Makoto","family":"Nakajima","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Kumamoto University  5-1 Oe-honmachi, Chuo-ku Kumamoto 862-0973 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,2,10]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.07.002"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0024-3205(90)90507-N"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb1961.36.318"},{"key":"e_1_2_8_5_1","unstructured":"\u00a0"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104557"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00067"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm201243p"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1528-1167.2005.00326.x"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2006.06.043"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.3229"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-200060020-00009"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800920"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201002183"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.08.046"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905329"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300489q"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202200041"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201902817"},{"key":"e_1_2_8_21_1","unstructured":"\u00a0"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501275"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800506"},{"key":"e_1_2_8_24_1","unstructured":"\u00a0"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0752585"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9052653"},{"key":"e_1_2_8_27_1","unstructured":"\u00a0"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201602230"},{"key":"e_1_2_8_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201602230"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202200215"},{"key":"e_1_2_8_30_1","unstructured":"\u00a0"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201300004"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1340600"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2019.151421"},{"key":"e_1_2_8_34_1","unstructured":"\u00a0"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810599"},{"key":"e_1_2_8_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201810599"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201501080"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol502269w"},{"key":"e_1_2_8_38_1","unstructured":"\u00a0"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.03.095"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc31543b"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202000914"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/1522-2675(20000809)83:8<1846::AID-HLCA1846>3.0.CO;2-V"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja047339w"},{"key":"e_1_2_8_44_1","unstructured":"Nonlinear effect (NLE) was not observed in the reaction of5\u2009cand6\u2009a; see supplementally information."},{"key":"e_1_2_8_45_1","unstructured":"CCDC 2216224 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge viawww.ccdc.cam.ac.uk\/data\u2002request\/cif or by emailing data\u2002request@ccdc.cam.ac.uk or by contacting The Cambridge Crystallographic Data Centre 12 Union Road Cambridge CB2 1EZ UK; fax: +44 1223 336033."},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00508-8"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01445"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2021.130545"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203506","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202203506","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203506","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:42:12Z","timestamp":1760290932000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202203506"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,10]]},"references-count":50,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2023,3,13]]}},"alternative-id":["10.1002\/chem.202203506"],"URL":"https:\/\/doi.org\/10.1002\/chem.202203506","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,10]]},"assertion":[{"value":"2022-11-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-02-10","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202203506"}}