{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:21:25Z","timestamp":1760548885503},"reference-count":29,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2009,12,10]],"date-time":"2009-12-10T00:00:00Z","timestamp":1260403200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2010,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The reduction of the axially chiral <jats:italic>N<\/jats:italic>\u2010(<jats:italic>o<\/jats:italic>\u2010aryl)\u20105,5\u2010dimethyl\u20102,4\u2010oxazolidinediones by NaBH<jats:sub>4<\/jats:sub> yielded axially chiral <jats:italic>N<\/jats:italic>\u2010(<jats:italic>o<\/jats:italic>\u2010aryl)\u20104\u2010hydroxy\u20105,5\u2010dimethyl\u20102\u2010oxazolidinone enantiomers having a chiral center at C\u20104, with 100% diastereoselectivity as has been shown by their <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C NMR spectra and by enantioselective HPLC analysis. The resolved enantiomeric isomers were found to interconvert thermally through an aldehyde intermediate formed upon ring cleavage via a latent ring\u2010chain\u2010ring tautomerization. It was found that the rate of enantiomerization depended on the size and the electronic effect of the <jats:italic>ortho<\/jats:italic> substituent present on the aryl ring bonded to the nitrogen of the heterocycle. Chirality 2010. \u00a9 2009 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20811","type":"journal-article","created":{"date-parts":[[2009,12,10]],"date-time":"2009-12-10T21:01:52Z","timestamp":1260478912000},"page":"641-654","source":"Crossref","is-referenced-by-count":14,"title":["Axially chiral <i>N<\/i>\u2010(<i>o<\/i>\u2010aryl)\u20104\u2010hydroxy\u20102\u2010oxazolidinone derivatives from diastereoselective reduction of <i>N<\/i>\u2010(<i>o<\/i>\u2010aryl)\u20102,4\u2010oxazolidinediones: Thermally interconvertible atropisomers via ring\u2010chain\u2010ring tautomerization"],"prefix":"10.1002","volume":"22","author":[{"given":"\u00d6znur","family":"Demir\u2010Ordu","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u0130lknur","family":"Do\u01e7an","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,12,10]]},"reference":[{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10189"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2003.12.039"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2005.09.019"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2008.09.001"},{"key":"e_1_2_6_6_2","first-page":"45","volume-title":"Reductions by the alumino\u2010 and borohydrides in organic synthesis","author":"Seyden\u2010Penne J","year":"1997"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(96)01157-X"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199709491"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00087-4"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020025b"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200210)2002:20<3447::AID-EJOC3447>3.0.CO;2-L"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01521-4"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4684-4883-2"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1070\/RC1982v051n08ABEH002911"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/a706380f"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00148-0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.05.092"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.05.058"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600447"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570440635"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.04.074"},{"key":"e_1_2_6_22_2","first-page":"501","volume-title":"Physical chemistry","author":"Alberty RA","year":"1992"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00256a032"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0165-022X(02)00123-9"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0165-022X(02)00118-5"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo020070j"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0355810"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/ct9150701080"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)88256-9"},{"key":"e_1_2_6_30_2","first-page":"305","volume-title":"Basic one\u2010 and two dimensional NMR spectroscopy","author":"Friebolin H","year":"2005"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.20811","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.20811","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T09:36:25Z","timestamp":1697448985000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.20811"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,12,10]]},"references-count":29,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2010,7]]}},"alternative-id":["10.1002\/chir.20811"],"URL":"https:\/\/doi.org\/10.1002\/chir.20811","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,12,10]]}}}