{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T23:12:24Z","timestamp":1762125144628,"version":"build-2065373602"},"reference-count":26,"publisher":"Wiley","issue":"18","license":[{"start":{"date-parts":[[2009,9,10]],"date-time":"2009-09-10T00:00:00Z","timestamp":1252540800000},"content-version":"vor","delay-in-days":9,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J of Separation Science"],"published-print":{"date-parts":[[2009,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A simple and rapid HPLC method using a polysaccharide\u2010based chiral stationary phase (Chiralpak AD\u2010H) in polar\u2010organic phase mode has been developed for direct resolution of glycidyl nitrobenzoate (GNB) and 2\u2010methyl glycidyl nitrobenzoate (MGNB) enantiomers. ACN and methanol were used as mobile phase and the effects of the addition of ethanol and 2\u2010propanol as organic modifier in the mobile phase, flow rate and the column temperature were tested. The optimized conditions were: methanol\/ethanol (80:20) at a flow rate of 0.9 mL\/min and 40\u00b0C. Analysis time was \u2a8713 min and the chiral resolution was \u2a882. The method was validated and resulted to be selective, precise and accurate. The method was found to be linear in 2\u2013300 \u03bcg\/mL range (<jats:italic>R<\/jats:italic><jats:sup>2 <\/jats:sup>&gt;0.999) with an LOD nearly 0.5 \u03bcg\/mL for four enantiomers. GNB and MGNB enantiomers were obtained by asymmetric epoxidation of allyl alcohol and 2\u2010methyl allyl alcohol, respectively, using chiral titanium\u2013tartrate complexes as catalyst and dichloromethane as solvent after <jats:italic>in situ<\/jats:italic> derivatization of the intermediate glycidols derivatives. The quite simple and rapid validated method was applied successfully for direct determination of the enantiomeric excess (\u2a8890%) and yield obtained in real samples of asymmetric epoxidation of allylic alcohols without further purification, workup or solvent removal. The method provides a useful and value\u2010added tool for controlling the enantiomeric purity of the synthesized epoxides.<\/jats:p>","DOI":"10.1002\/jssc.200900170","type":"journal-article","created":{"date-parts":[[2009,9,10]],"date-time":"2009-09-10T14:17:53Z","timestamp":1252592273000},"page":"3055-3063","source":"Crossref","is-referenced-by-count":3,"title":["HPLC with polysaccharide chiral stationary phase in polar\u2010organic phase mode: Application to the asymmetric epoxidation of allylic alcohols"],"prefix":"10.1002","volume":"32","author":[{"given":"Sonia","family":"Morante\u2010Zarcero","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isabel","family":"del Hierro","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariano","family":"Fajardo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isabel","family":"Sierra","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,9,10]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1984-30921"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00004a001"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00109a004"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)00758-7"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9618278"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02520-9"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(01)00230-0"},{"key":"e_1_2_1_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00538a077"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00253a032"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0172518"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016779"},{"key":"e_1_2_1_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(00)00950-X"},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(00)00501-X"},{"key":"e_1_2_1_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2004.06.087"},{"key":"e_1_2_1_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2006.03.019"},{"key":"e_1_2_1_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(03)01262-7"},{"key":"e_1_2_1_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0731-7085(01)00648-3"},{"key":"e_1_2_1_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac00279a055"},{"key":"e_1_2_1_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2007.06.008"},{"key":"e_1_2_1_21_2","unstructured":"Yashima E. Okamoto Y. in: Aboul\u2010Enein H. Y. Wainer I. W. (Eds.) The Impact of Stereochemistry on Drug Development and Use Chapter 12 (Chemical Analysis Series Vol. 142) John Wiley & Sons Inc. New York 1997 p. 345."},{"key":"e_1_2_1_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)01573-4"},{"key":"e_1_2_1_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)01060-3"},{"key":"e_1_2_1_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)01059-7"},{"key":"e_1_2_1_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2008.04.034"},{"key":"e_1_2_1_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(00)00949-3"},{"key":"e_1_2_1_27_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1988.1125"}],"container-title":["Journal of Separation Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjssc.200900170","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jssc.200900170","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T11:19:40Z","timestamp":1760872780000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jssc.200900170"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,9]]},"references-count":26,"journal-issue":{"issue":"18","published-print":{"date-parts":[[2009,9]]}},"alternative-id":["10.1002\/jssc.200900170"],"URL":"https:\/\/doi.org\/10.1002\/jssc.200900170","archive":["Portico"],"relation":{},"ISSN":["1615-9306","1615-9314"],"issn-type":[{"type":"print","value":"1615-9306"},{"type":"electronic","value":"1615-9314"}],"subject":[],"published":{"date-parts":[[2009,9]]}}}