{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T13:32:50Z","timestamp":1760707970962,"version":"build-2065373602"},"reference-count":78,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2008,8,21]],"date-time":"2008-08-21T00:00:00Z","timestamp":1219276800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Adv Synth Catal"],"published-print":{"date-parts":[[2008,9,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This paper presents a new and more sustainable alternative approach for the Sharpless catalytic asymmetric dihydroxylation (AD) of olefins using a water\/surfactant system as reaction media. The AD reaction was performed using several cationic and anionic surfactants allowing yields and enantiomeric excesses higher or comparable with the conventional systems (using organic mixtures). The use of this water\/surfactant medium offers the additional advantage of performing the reactions without the need of a slow addition of olefins. Asymmetric dihydroxylation of 1\u2010hexene in a 1.5\u2005mM sodium cholate aqueous solution, using <jats:italic>N<\/jats:italic>\u2010methylmorpholine <jats:italic>N<\/jats:italic>\u2010oxide (NMO) as co\u2010oxidant was selected as model system to evaluate the feasibility of recycling the Sharpless catalytic system by nanofiltration. The reaction media was processed by nanofiltration, the product was isolated in the permeate, whereas the catalytic system and surfactant were retained by the membrane and recycled through six successive reactions, improving the catalyst turn\u2010over number. The experimental results were compared with the ones calculated on the basis of mass balances, membrane rejections to product and reaction yields.<\/jats:p>","DOI":"10.1002\/adsc.200800269","type":"journal-article","created":{"date-parts":[[2008,8,21]],"date-time":"2008-08-21T09:16:18Z","timestamp":1219310178000},"page":"2086-2098","source":"Crossref","is-referenced-by-count":14,"title":["Sharpless Asymmetric Dihydroxylation of Olefins in WaterSurfactant Media with Recycling of the Catalytic System by Membrane Nanofiltration"],"prefix":"10.1002","volume":"350","author":[{"given":"Luis\u2005C.","family":"Branco","sequence":"first","affiliation":[]},{"given":"Frederico Castelo","family":"Ferreira","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9\u2005L.","family":"Santos","sequence":"additional","affiliation":[]},{"given":"Jo\u00e3o\u2005G.","family":"Crespo","sequence":"additional","affiliation":[]},{"given":"Carlos A.\u2005M.","family":"Afonso","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2008,8,29]]},"reference":[{"key":"e_1_2_2_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471721506.ch12"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471721506.ch11"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a009"},{"key":"e_1_2_2_4_2","first-page":"1725","author":"Zaitsev A. B.","year":"2006","journal-title":"Synthesis"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505252"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00105a065"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/op970030v"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/op000035j"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200304828"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/op025622e"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1615-4169(200206)344:3\/4<421::AID-ADSC421>3.0.CO;2-F"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200606210"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja993099m"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0161965"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200202199"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol020225"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016101u"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017889j"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo026687i"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200303114"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010202)40:3<586::AID-ANIE586>3.0.CO;2-L"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/b305154b"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol027109r"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/la990578q"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200404112"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.5012\/bkcs.2005.26.11.1839"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199707411"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar990140h"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01105-4"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol010096h"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200303114"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2004.03.040"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol026172d"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01461-2"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/b208631j"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/b210104c"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035588h"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2004.01.011"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/b411325j"},{"key":"e_1_2_2_40_2","unstructured":"L.\u2005C. Branco A. Serbanovic M.\u2005N. da Ponte C.\u2005A.\u2005M. Afonso Patent ApplicationsPT 10293703 and PCT\/PT2005\/000007;"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.04.025"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/B403333G"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.04.025"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/B600816J"},{"key":"e_1_2_2_45_2","first-page":"10","author":"Ferreira F. C.","year":"2007","journal-title":"Tetrahedron: Asymmetry"},{"volume-title":"Organic Reactions in Aqueous Media","year":"1997","author":"Li C. J.","key":"e_1_2_2_46_2"},{"volume-title":"Aqueous\u2010Phase Organometallic Catalysis","year":"1998","author":"Cornils B.","key":"e_1_2_2_47_2"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-94-011-4950-1_8"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/B507207G"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030009u"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010122p"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1994-25562"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604952"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470988817"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(96)00669-2"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/ep.3300070116"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/cite.330710304"},{"key":"e_1_2_2_58_2","unstructured":"C.\u2005H.Linder M.Nemas M.Perry R.Katraro US Patent 5 265 734 1993;"},{"key":"e_1_2_2_59_2","unstructured":"L.\u2005S.White I.Wang Minhas S.Bhupender US Patent 5 264 166 1993;"},{"key":"e_1_2_2_60_2","first-page":"205","author":"White L. S.","year":"2002","journal-title":"J. Membrane Sci."},{"journal-title":"Advanced Membrane Technology","first-page":"984","author":"Bhanushali D.","key":"e_1_2_2_61_2"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0100778"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01734-8"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/b009898l"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/b602184k"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1395(199808\/09)11:8\/9<584::AID-POC59>3.0.CO;2-F"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.2116\/analsci.14.379"},{"key":"e_1_2_2_68_2","unstructured":"value to be found at:http:\/\/www.sigmaaldrich.com\/catalog\/search\/ProductDetail\/SIAL\/C5070."},{"key":"e_1_2_2_69_2","unstructured":"Reaction yield (Yreact): Yreact(%)=${{{\\rm diol}\\ {\\rm produced}\\ ({\\rm mol})\\over {\\rm olefin}\/{\\rm substrate}\\ {\\rm added}\\ ({\\rm mol})}}$\u00d7100; reaction process (Yprocess): Yprocess(%)=${{{\\rm diol}\\ {\\rm in}\\ {\\rm permeate}\\ ({\\rm mol})\\over {\\rm olefin}\/{\\rm substrate}\\ {\\rm added}\\ ({\\rm mol})}}$\u00d7100."},{"key":"e_1_2_2_70_2","unstructured":"Specific yield: (Yreact): R\u2010Yield (%)=${{{\\rm diol}\\ ({\\rm mol})\\over {\\rm substrate}\\ {\\rm added}\\ ({\\rm mol})}}$\u00d7100=${{{\\rm Y}{_{{\\rm react}}}\\ (\\char37 )\\over 2}}$(1+${{ee\\ (\\char37 )\\over 100}}$)."},{"volume-title":"Exploring QSAR \u2013 Hydrophobic, Electronic, and Steric Constants","year":"1995","author":"Hansch C.","key":"e_1_2_2_71_2"},{"key":"e_1_2_2_72_2","unstructured":"Turn\u2010over number (TON): TON(i)=${{{{}\\mathrel{\\mathop{\\sum{}}\\limits^{n}\\limits_{j=1}}{}}{\\rm diol}\\ {\\rm in}\\ {\\rm permeate}\\ ({\\rm j})\\ ({\\rm mol})\\over {\\rm Catalyst}\\ {\\rm added}\\ {\\rm in}\\ {\\rm 1st}\\ {\\rm cycle}\\ ({\\rm Os}\\ {\\rm mol})}}$."},{"key":"e_1_2_2_73_2","unstructured":"Molecular weight cut\u2010off (MWCO) of a membrane is the molecular weight of the solute which 90% is rejected by the membrane."},{"key":"e_1_2_2_74_2","unstructured":"Rejection (Rej): Rej (%)=(1\u2212${{[{\\rm Solute}]{_{{\\rm permeate}}}\\over [{\\rm Solute}]{_{{\\rm feed}}}}}$)\u00d7100; in this study the solute is either osmium or diol."},{"key":"e_1_2_2_75_2","unstructured":"A stainless steel MetCell with a membrane area of 0.0052\u2005m2purchased from Membrane Extraction Technology Ltd. UK was used as nanofiltration equipment. Details on equipment to be found underhttp:\/\/www.membrane\u2010extraction\u2010technology.com\/METCell.php."},{"key":"e_1_2_2_76_2","unstructured":"NMO\/S S\/Os and L\/Os were maintained at about 1.5 187 and 2.0 mol\u22c5mol\u22121 respectively."},{"key":"e_1_2_2_77_2","unstructured":"Osmium in permeate (%)=${{{\\rm permeate}\\ ({\\rm mL})\\times {\\rm osmium}\\ {\\rm in}\\ {\\rm permeate}\\ ({\\rm nM})\\over {\\rm osmium}\\ {\\rm added}\\ ({{\\rm \\mu}}{\\rm mol})}}$\u00d7100."},{"key":"e_1_2_2_78_2","first-page":"71","author":"Donohoe T. J.","year":"2006","journal-title":"J. Org. Chem."}],"container-title":["Advanced Synthesis &amp; Catalysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fadsc.200800269","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/adsc.200800269","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T20:29:37Z","timestamp":1759782577000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/adsc.200800269"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,8,29]]},"references-count":78,"journal-issue":{"issue":"13","published-print":{"date-parts":[[2008,9,5]]}},"alternative-id":["10.1002\/adsc.200800269"],"URL":"https:\/\/doi.org\/10.1002\/adsc.200800269","archive":["Portico"],"relation":{},"ISSN":["1615-4150","1615-4169"],"issn-type":[{"type":"print","value":"1615-4150"},{"type":"electronic","value":"1615-4169"}],"subject":[],"published":{"date-parts":[[2008,8,29]]}}}