{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T13:31:02Z","timestamp":1760707862596,"version":"build-2065373602"},"reference-count":78,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2007,8,23]],"date-time":"2007-08-23T00:00:00Z","timestamp":1187827200000},"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":[[2007,11,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A synthetic route to tetradentate chiral N<jats:sub>4<\/jats:sub> ligands has been developed with the aim to study the potential of corresponding iron and manganese complexes as catalysts for enantioselective epoxidation. These ligands, which contain two oxazoline rings and two trialkylamino groups as coordinating units, are readily prepared in enantiomerically pure form by the reaction of chiral 2\u2010chloromethyloxazolines with achiral <jats:italic>N<\/jats:italic>,<jats:italic>N\u2032<\/jats:italic>\u2010dimethylethane\u20101,2\u2010diamine or chiral (<jats:italic>R<\/jats:italic>,<jats:italic>R<\/jats:italic>)\u2010<jats:italic>N<\/jats:italic>,<jats:italic>N\u2032<\/jats:italic>\u2010dimethylcyclohexane\u20101,2\u2010diamine. The ligands derived from <jats:italic>N<\/jats:italic>,<jats:italic>N\u2032<\/jats:italic>\u2010dimethylethane\u20101,2\u2010diamine reacted with anhydrous metal halides MnCl<jats:sub>2<\/jats:sub> and FeCl<jats:sub>2<\/jats:sub> in a stereoselective manner to give octahedral mononuclear complexes that have the general formula <jats:italic>\u0394<\/jats:italic>\u2010[(L)MCl<jats:sub>2<\/jats:sub>]. In contrast, the ligands derived from <jats:italic>N<\/jats:italic>,<jats:italic>N\u2032<\/jats:italic>\u2010dimethylcyclohexane\u20101,2\u2010diamine formed complexes with different coordination modes depending on the diastereomer employed: in one case the metal ion was found to be pentacoordinate, in the other case a hexacoordinated complex was observed. The structure of a series of Fe and Mn complexes was determined by X\u2010ray analysis. The coordination chemistry of these ligands was further studied by X\u2010ray and NMR analyses of the diamagnetic isostructural complexes [(L)ZnCl<jats:sub>2<\/jats:sub>]. Analogous ionic complexes, which were prepared by removing chloride with silver trifluoromethanesulfonate or hexafluoroantimonate, were tested as catalysts for the epoxidation of olefins.<\/jats:p>","DOI":"10.1002\/chem.200700826","type":"journal-article","created":{"date-parts":[[2007,8,24]],"date-time":"2007-08-24T22:24:33Z","timestamp":1187994273000},"page":"8960-8970","source":"Crossref","is-referenced-by-count":41,"title":["Synthesis and Metal Complexes of Chiral <i>C<\/i><sub>2<\/sub>\u2010Symmetric Diamino\u2013Bisoxazoline Ligands"],"prefix":"10.1002","volume":"13","author":[{"given":"Geoffroy","family":"Guillemot","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Markus","family":"Neuburger","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"Pfaltz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2007,10,24]]},"reference":[{"volume-title":"Biomimetic Oxidations Catalyzed by Transition Metal Complexes","year":"2000","key":"e_1_2_6_1_2"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"volume-title":"Cytochrome P450: Structure, Mechanism, and Biochemistry","year":"1995","key":"e_1_2_6_3_2"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020443g"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00498a040"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00515a063"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)92196-8"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"volume-title":"Comprehensive Organometallic Chemistry II: A Review of the Literature 1982\u20131994, Vol. 12","year":"1995","author":"Murahashi S. I.","key":"e_1_2_6_9_2"},{"volume-title":"The Porphyrin Handbook","year":"2000","key":"e_1_2_6_10_2"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-008046519-7.00137-4"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00163a052"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)88562-7"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306945"},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9500489"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020622y"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1999.3462"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1078020"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020628n"},{"key":"e_1_2_6_23_2","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja029962r"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol048846l"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2006.01.042"},{"key":"e_1_2_6_27_2","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja015884g"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/a703542j"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961287e"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020471z"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200501262"},{"key":"e_1_2_6_32_3","doi-asserted-by":"publisher","DOI":"10.1039\/B511331H"},{"key":"e_1_2_6_33_2","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1999-3122"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9900865"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0307152101"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(19980515)4:5<818::AID-CHEM818>3.0.CO;2-#"},{"key":"e_1_2_6_37_3","doi-asserted-by":"publisher","DOI":"10.1039\/a708874d"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040642v"},{"key":"e_1_2_6_39_2","unstructured":"\u00a0"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00254a054"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-98-8407"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91946-X"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397919208021650"},{"key":"e_1_2_6_44_2","unstructured":"T.\u2005A.Chamberlin US\u2010A 3962235 1996["},{"key":"e_1_2_6_44_3","first-page":"160113x","volume":"85","year":"1976","journal-title":"Chem. Abstr."},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971161x"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200501500"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1081\/SCC-120014777"},{"key":"e_1_2_6_48_2","unstructured":"For fluorine transfer reactions of this type see:"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00267a068"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1080\/02603598208078105"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00026a012"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(00)84981-6"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00080a027"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00096a040"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/a901678c"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(99)00502-2"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010302)113:5<975::AID-ANGE975>3.0.CO;2-P"},{"key":"e_1_2_6_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010302)40:5<949::AID-ANIE949>3.0.CO;2-4"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0120025"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200200694"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200600453"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0682(200104)2001:4<1057::AID-EJIC1057>3.0.CO;2-A"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/om0340443"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja015601k"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/DT9840001349"},{"volume-title":"Purification of Laboratory Chemicals","year":"1996","author":"Armarego W. L. F.","key":"e_1_2_6_65_2"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)92903-X"},{"key":"e_1_2_6_67_2","unstructured":"N. End PhD Thesis University of Basel (Switzerland) 1997and ref.\u2005[12c]."},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.080.0009"},{"key":"e_1_2_6_69_2","unstructured":"B.\u2005V. Nonius COLLECT Software 1997\u20132001."},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889894000221"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889803021800"},{"key":"e_1_2_6_72_2","unstructured":"\u00a0"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4684-0136-3"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767393012784"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200700826","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200700826","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T11:01:39Z","timestamp":1760266899000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200700826"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,10,24]]},"references-count":78,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2007,11,5]]}},"alternative-id":["10.1002\/chem.200700826"],"URL":"https:\/\/doi.org\/10.1002\/chem.200700826","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2007,10,24]]}}}