{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T14:54:11Z","timestamp":1791298451042,"version":"4.1.0"},"reference-count":118,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2013,12,11]],"date-time":"2013-12-11T00:00:00Z","timestamp":1386720000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2014,1,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>\u03b1\u2010Fluoroalkenoates and 4\u2010fluoro\u20105\u2010isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (<jats:italic>E<\/jats:italic>)\u2010\u03b1\u2010fluoroalkenoates and 4\u2010fluoro\u20105\u2010isoxazolidinones by the reactions between nitrones and \u03b1\u2010fluoro\u2010\u03b1\u2010bromoacetate. By altering N\u2010substituents in nitrones, (<jats:italic>E<\/jats:italic>)\u2010\u03b1\u2010fluoroalkenoates and 4\u2010fluoro\u20105\u2010isoxazolidinones can be achieved, respectively, with high chemo\u2010 and stereoselectivities. Experimental and computational studies have been conducted to elucidate the reaction mechanisms. Linear free energy relationship studies further revealed that the N\u2010substituent effects are primarily of electronic origin.<\/jats:p>","DOI":"10.1002\/chem.201303509","type":"journal-article","created":{"date-parts":[[2013,12,11]],"date-time":"2013-12-11T08:53:48Z","timestamp":1386752028000},"page":"831-838","source":"Crossref","is-referenced-by-count":20,"title":["Stereoselective Synthesis of Fluoroalkenoates and Fluorinated Isoxazolidinones: N\u2010Substituents Governing the Dual Reactivity of Nitrones"],"prefix":"10.1002","volume":"20","author":[{"given":"G. K. Surya","family":"Prakash","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhe","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fang","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Rahm","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chuanfa","family":"Ni","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marc","family":"Iuliucci","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ralf","family":"Haiges","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"George A.","family":"Olah","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,12,11]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For reviews on recent developments in synthetic organofluorine chemistry"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar700149s"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800221v"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2008.11.011"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b916463d"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/B909566G"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.6.65"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr1004293"},{"key":"e_1_2_6_9_2","first-page":"770","author":"Ni C.","year":"2011","journal-title":"Synlett"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527664801.ch12"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206566"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1139(01)00375-X"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/B610213C"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.09.65"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1131943"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470281895"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1038\/263110a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00195a010"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-2964(79)90019-7"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/0223-5234(93)90145-5"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)02269-4"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106187a"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/co9950200251"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(96)00311-0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1139(95)03255-C"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)01267-1"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1139(97)00134-6"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)01363-4"},{"key":"e_1_2_6_32_2","first-page":"7800","volume":"69","author":"Ichikawa J.","year":"2004","journal-title":"J. Org. Chem."},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9610004033"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/j39670002206"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1975-23683"},{"key":"e_1_2_6_36_2","first-page":"2376","volume":"15","author":"Ren A.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_6_37_2","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00155a001"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00341a070"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00295a046"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00302a030"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)60990-5"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)81105-4"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00102a038"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1218789"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2010.04.113"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200905077"},{"key":"e_1_2_6_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905077"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol100090r"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1997-3228"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2005.07.011"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol8029627"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2010.06.009"},{"key":"e_1_2_6_53_2","unstructured":"\u00a0"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)02218-X"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1780"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.50.706"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)02135-9"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990178u"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1139(95)03382-3"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800194"},{"key":"e_1_2_6_61_2","unstructured":"Pioneering work using nitrones in olefin synthesis see"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)02025-1"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200209)2002:17<2961::AID-EJOC2961>3.0.CO;2-F"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035360u"},{"key":"e_1_2_6_65_2","unstructured":"\u00a0"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50138a002"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29770001898"},{"key":"e_1_2_6_68_2","unstructured":"Oxamate bio"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00243a014"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1039\/B514147H"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.02.066"},{"key":"e_1_2_6_72_2","unstructured":"Nitrile Oxides Nitrones and Nitronates in Organic Synthesis 2nd Ed. (Ed.: H. Feuer) Wiley Hoboken 2008 129\u2013434."},{"key":"e_1_2_6_73_2","unstructured":"\u00a0"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.19763091115"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(79)87010-6"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971009v"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1039\/a809958h"},{"key":"e_1_2_6_78_2","first-page":"48","author":"Merino P.","year":"2004","journal-title":"Arkivoc"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.12.004"},{"key":"e_1_2_6_80_2","unstructured":"For discussions on the instability of \u03b1\u2010fluorocarbanions"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00972a065"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901414"},{"key":"e_1_2_6_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901414"},{"key":"e_1_2_6_83_2","first-page":"770","author":"Ni C.","year":"2011","journal-title":"Synlett"},{"key":"e_1_2_6_84_2","doi-asserted-by":"crossref","unstructured":"HMPA has been widely utilized in organolithium chemistry to enhance the reactivity of organolithium reagents. Robert R. Dykstra Hexamethylphosphoric Triamide in D. Crich A.\u2005B. Charette P.\u2005L. Fuchs G. Molander Eds. e\u2010EROS Encyclopedia of Reagents for Organic Synthesis: Wiley DOI: 10.1002\/047084289X.rh020.","DOI":"10.1002\/047084289X.rh020"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01141a006"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(78)89004-8"},{"key":"e_1_2_6_87_2","unstructured":"The proposed \u03b1\u2010deprotonation ofN\u2010alkyl groups in nitrones can be inferred by the high acidity of the \u03b1\u2010proton onN\u2010alkyl groups in imines"},{"key":"e_1_2_6_88_2","first-page":"8520","volume":"120","author":"O\u2019Donnell M. J.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60230a006"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00905a018"},{"key":"e_1_2_6_91_2","unstructured":"Stamm et\u2005al. have previously reported a similar Reformatsky\u2010type reaction between nitrones and \u03b1\u2010bromoacetates to form 5\u2010isoxazolidinones see 12[b]."},{"key":"e_1_2_6_92_2","unstructured":"It has been reported that theN\u2010tert\u2010butyl group and otherN\u2010tertiary substitutes can be selectively removed in the presence of triflic acid which allows further transformations of isoxazolidinones;"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00200a009"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1990-21189"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990846b"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0618609"},{"key":"e_1_2_6_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00030a007"},{"key":"e_1_2_6_98_2","doi-asserted-by":"publisher","DOI":"10.1139\/v89-265"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9560003416"},{"key":"e_1_2_6_100_2","unstructured":"Gaussian\u200509 RevisionD.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005A. Montgomery \u2005Jr. J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels \u00d6. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski and D.\u2005J. Fox Gaussian Inc. Wallingford CT 2009."},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_6_102_2","unstructured":"\u00a0"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1016\/0301-0104(81)85090-2"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3359469"},{"key":"e_1_2_6_105_2","unstructured":"Selected computational studies on nitrone\u2013olefin and nitrone\u2013enolate [3+2]cycloaddition reactions see"},{"key":"e_1_2_6_106_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.11.121"},{"key":"e_1_2_6_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja300002k"},{"key":"e_1_2_6_108_2","unstructured":"CCDC\u2010958856 (5\u2009a) 958855 (6\u2009a) and 958850 (7\u2009e) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_6_109_2","unstructured":"\u00a0"},{"key":"e_1_2_6_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100894a011"},{"key":"e_1_2_6_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100862a050"},{"key":"e_1_2_6_112_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470171813.ch6"},{"key":"e_1_2_6_113_2","unstructured":"\u00a0"},{"key":"e_1_2_6_114_2","first-page":"455","volume-title":"Modern Physical Organic Chemistry","author":"Anslyn E. V.","year":"2006"},{"key":"e_1_2_6_115_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470171912.ch4"},{"key":"e_1_2_6_116_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00839a047"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201303509","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201303509","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:16:05Z","timestamp":1760285765000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201303509"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,12,11]]},"references-count":118,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2014,1,13]]}},"alternative-id":["10.1002\/chem.201303509"],"URL":"https:\/\/doi.org\/10.1002\/chem.201303509","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,12,11]]}}}