{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,13]],"date-time":"2026-02-13T15:16:09Z","timestamp":1770995769759,"version":"3.50.1"},"reference-count":157,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2010,1,14]],"date-time":"2010-01-14T00:00:00Z","timestamp":1263427200000},"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":[[2010,2,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Previously unexplored enantiopure zwitterionic ammonium dienolates have been utilized in this work as reactive intermediates that act as diene components in hetero\u2010Diels\u2013Alder reactions (HDAs) with aldehydes to produce optically active \u03b4\u2010lactones, subunits of numerous bioactive products. The dienolates were generated in situ from <jats:italic>E<\/jats:italic>\/<jats:italic>Z<\/jats:italic> mixtures of \u03b1,\u03b2\u2010unsaturated acid chlorides by use of a nucleophilic quinidine derivative and Sn(OTf)<jats:sub>2<\/jats:sub> as co\u2010catalyst. The latter component was not directly involved in the cycloaddition step with aldehydes and simply facilitated the formation of the reactive dienolate species. The scope of the cycloaddition was considerably improved by use of a complex formed from Er(OTf)<jats:sub>3<\/jats:sub> and a simple commercially available norephedrine\u2010derived ligand that tolerated a broad range of aromatic and heteroaromatic aldehydes for a cooperative bifunctional Lewis\u2010acid\u2010\/Lewis\u2010base\u2010catalyzed reaction, providing \u03b1,\u03b2\u2010unsaturated \u03b4\u2010lactones with excellent enantioselectivities. Mechanistic studies confirmed the formation of the dienolate intermediates for both catalytic systems. The active Er<jats:sup>III<\/jats:sup> complex is most likely a monomeric species. Interestingly, all lanthanides can catalyze the title reaction, but the efficiency in terms of yield and enantioselectivity depends directly on the radius of the Ln<jats:sup>III<\/jats:sup> ion. Similarly, use of the pseudolanthanides Sc<jats:sup>III<\/jats:sup> and Y<jats:sup>III<\/jats:sup> also resulted in product formation, whereas the larger La<jats:sup>III<\/jats:sup> and other transition metal salts, as well as main group metal salts, proved to be inefficient. In addition, various synthetic transformations of 6\u2010CCl<jats:sub>3<\/jats:sub>\u2010 or 4\u2010silyl\u2010substituted \u03b1,\u03b2\u2010unsaturated \u03b4\u2010lactones, giving access to a number of valuable \u03b4\u2010lactone building blocks, were investigated.<\/jats:p>","DOI":"10.1002\/chem.200902896","type":"journal-article","created":{"date-parts":[[2010,1,14]],"date-time":"2010-01-14T14:44:23Z","timestamp":1263480263000},"page":"2503-2517","source":"Crossref","is-referenced-by-count":64,"title":["Catalytic Asymmetric Formation of \u03b4\u2010Lactones from Unsaturated Acyl Halides"],"prefix":"10.1002","volume":"16","author":[{"given":"Paolo\u2005S.","family":"Tiseni","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ren\u00e9","family":"Peters","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2010,2,15]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20001016)112:20<3702::AID-ANGE3702>3.0.CO;2-R"},{"key":"e_1_2_6_1_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20001016)39:20<3558::AID-ANIE3558>3.0.CO;2-I"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00361a042"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00033a005"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)60892-4"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00209a061"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00184a087"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00124a001"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971758c"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19990816)111:16<2549::AID-ANGE2549>3.0.CO;2-H"},{"key":"e_1_2_6_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990816)38:16<2398::AID-ANIE2398>3.0.CO;2-E"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502176"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502176"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028186k"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0172518"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)86747-2"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.44.66"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm990281p"},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00482-6"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50076a017"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867023368809"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja051185i"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/B514147H"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00128a032"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00382a001"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1059344"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr940368c"},{"key":"e_1_2_6_26_2","unstructured":"\u00a0"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049364c"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo060046w"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol8002282"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0168317"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja051573k"},{"key":"e_1_2_6_32_2","unstructured":"For the described example and selected references about hydrogen\u2010bonding activation see"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400515"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo060129c"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01257a030"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700859"},{"key":"e_1_2_6_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700859"},{"key":"e_1_2_6_37_2","unstructured":"Selected 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Attempts to extend the reaction scope to unactivated carbonyl compounds failed even employing Lewis acids to promote the cycloaddition which only caused decomposition of the ketene."},{"key":"e_1_2_6_65_2","unstructured":"\u00a0"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9600000001"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)83371-8"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01257a030"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19730001514"},{"key":"e_1_2_6_70_2","first-page":"1409","author":"Gelin R.","year":"1973","journal-title":"Bull. Soc. Chim. Fr."},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19830660744"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)94015-2"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80823-6"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/B312682J"},{"key":"e_1_2_6_75_2","unstructured":"Review articles:"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020061a"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0683764"},{"key":"e_1_2_6_78_2","unstructured":"\u00a0"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19606340103"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1007\/BFb0071301"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19697220102"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja044179f"},{"key":"e_1_2_6_83_2","unstructured":"B.\u2005G.Jackson Swiss Patent CH681302\u2009A5 1993."},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00120-2"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja045971j"},{"key":"e_1_2_6_86_2","unstructured":"Theoretical studies of HDA reactions have revealed that the mechanism can change from a concerted non\u2010synchronous to a stepwise mechanism depending on the substituents on the reacting species and on the reaction conditions. See for example:"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19891011031"},{"key":"e_1_2_6_87_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198913711"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00030a066"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00064a020"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1002\/poc.610071109"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980079w"},{"key":"e_1_2_6_92_2","unstructured":"\u00a0"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39840001181"},{"key":"e_1_2_6_94_2","unstructured":"see ref.\u2005[22n]."},{"key":"e_1_2_6_95_2","unstructured":"\u00a0"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(95)00125-9"},{"key":"e_1_2_6_97_2","first-page":"1505","author":"Koch F. M.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_6_98_2","unstructured":"For the synthetic utility of dichloromethyl groups see e.g.:"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo050342t"},{"key":"e_1_2_6_100_2","first-page":"546","author":"Arasaki H.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.09.098"},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)80457-9"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0109467"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01178-4"},{"key":"e_1_2_6_105_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(96)00038-5"},{"key":"e_1_2_6_106_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1975-23803"},{"key":"e_1_2_6_107_2","unstructured":"With a residue R2in24bulkier than Me enantioselectivity decreased to a large degree (e.g. R2=Et: 60\u2009%\u2005eewith1\u2009a; R2=nPr: 32\u2009%\u2005eewith1\u2009a). Similarly glyoxylates and other 1 2\u2010dicarbonyl dienophiles resulted in poor enantioselectivity."},{"key":"e_1_2_6_108_2","unstructured":"For the application of bifunctional catalysts in [2+2] cycloadditions of ketenes see for example: reference\u2005[22d e \u200929] and"},{"key":"e_1_2_6_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061979h"},{"key":"e_1_2_6_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0626903"},{"key":"e_1_2_6_111_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300635"},{"key":"e_1_2_6_111_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300635"},{"key":"e_1_2_6_112_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20021004)114:19<3704::AID-ANGE3704>3.0.CO;2-4"},{"key":"e_1_2_6_112_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20021004)41:19<3554::AID-ANIE3554>3.0.CO;2-P"},{"key":"e_1_2_6_113_2","unstructured":"For lanthanide complexes acting as bifunctional catalysts see for example:"},{"key":"e_1_2_6_114_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971091204"},{"key":"e_1_2_6_114_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199712361"},{"key":"e_1_2_6_115_2","doi-asserted-by":"publisher","DOI":"10.1039\/b203495f"},{"key":"e_1_2_6_116_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-869831"},{"key":"e_1_2_6_117_2","doi-asserted-by":"publisher","DOI":"10.1039\/b506346a"},{"key":"e_1_2_6_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800742d"},{"key":"e_1_2_6_119_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0079-6727(02)00025-3"},{"key":"e_1_2_6_120_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0567739476001551"},{"key":"e_1_2_6_121_2","unstructured":"Slow addition of the acid chloride substrates over 30\u2005min is recommended to maintain a low vinylketene concentration so as to minimize di\u2010 and oligomerization."},{"key":"e_1_2_6_122_2","unstructured":"The absolute configuration was determined by chemical correlation using a similar synthetic route as the one described in Scheme\u20053 (see the Supporting Information)."},{"key":"e_1_2_6_123_2","unstructured":"The enolizable dihydrocinnamaldehyde and cyclohexylcarbaldehyde as well as the non\u2010enolizable pivaldehyde resulted in complete aldehyde decomposition."},{"key":"e_1_2_6_124_2","unstructured":"Selected examples:"},{"key":"e_1_2_6_125_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2006.01.001"},{"key":"e_1_2_6_126_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2006.01.044"},{"key":"e_1_2_6_127_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462338"},{"key":"e_1_2_6_127_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462338"},{"key":"e_1_2_6_128_2","doi-asserted-by":"publisher","DOI":"10.1002\/0470010088"},{"key":"e_1_2_6_129_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200600357"},{"key":"e_1_2_6_130_2","unstructured":"Due to its employment in optical fibers ErIIIis currently about 4\u20135 times less expensive than YbIII."},{"key":"e_1_2_6_131_2","unstructured":"[Yb(NTf2)3] gave no conversion probably because of a poor solubility in the THF\/toluene solvent system."},{"key":"e_1_2_6_132_2","unstructured":"For other approaches by our group to selectively form quaternary stereocenters see:"},{"key":"e_1_2_6_133_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900712"},{"key":"e_1_2_6_134_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200803539"},{"key":"e_1_2_6_134_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200803539"},{"key":"e_1_2_6_135_2","first-page":"1495","author":"Xin Z.\u2010q.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_6_136_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702086"},{"key":"e_1_2_6_136_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702086"},{"key":"e_1_2_6_137_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-06-S(K)10"},{"key":"e_1_2_6_138_2","first-page":"5783","volume":"71","author":"Peters R.","year":"2006","journal-title":"J. Org. 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