{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T08:39:28Z","timestamp":1790843968422,"version":"4.1.0"},"reference-count":143,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2014,1,8]],"date-time":"2014-01-08T00:00:00Z","timestamp":1389139200000},"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":[[2014,2,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A procedure that enables high yielding access to phosphonic \u03b3\u2010(hydroxyalkyl)butenolides with excellent regio\u2010, diastereo\u2010 and enantiocontrol is reported. The simultaneous construction of up to two adjacent quaternary stereogenic centers by a catalytic asymmetric vinylogous Mukaiyama aldol reaction unites biologically and medicinally relevant entities, namely \u03b1\u2010hydroxy phosphonates and \u03b3\u2010(hydroxyalkyl)butenolides. This is achieved by utilizing a readily available chiral copper\u2010sulfoximine catalyst showing a broad functional group tolerance for both the electrophilic and nucleophilic reactants. A discussion about potential factors affecting the observed level of enantioselectivity, which stems from the enantiopure sulfoximine ligand, is also included.<\/jats:p>","DOI":"10.1002\/chem.201304331","type":"journal-article","created":{"date-parts":[[2014,1,8]],"date-time":"2014-01-08T15:29:39Z","timestamp":1389194979000},"page":"1691-1700","source":"Crossref","is-referenced-by-count":61,"title":["Catalytic, Asymmetric Synthesis of Phosphonic \u03b3\u2010(Hydroxyalkyl)butenolides with Contiguous Quaternary and Tertiary Stereogenic Centers"],"prefix":"10.1002","volume":"20","author":[{"given":"Marcus","family":"Frings","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isabelle","family":"Thom\u00e9","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ingo","family":"Schiffers","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fangfang","family":"Pan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carsten","family":"Bolm","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,1,8]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1038\/184901b0"},{"key":"e_1_2_6_2_2","unstructured":"For reviews see:"},{"key":"e_1_2_6_3_2","first-page":"5","volume-title":"The Role of Phosphonates in Living Systems","author":"Hilderbrand R. L.","year":"1983"},{"key":"e_1_2_6_4_2","first-page":"24","volume-title":"Biochemistry of Natural C\uf8ffP Compounds","author":"Horiguchi M.","year":"1984"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.biochem.78.091707.100215"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00701-2"},{"key":"e_1_2_6_7_2","unstructured":"For selected examples see:"},{"key":"e_1_2_6_8_2","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1016\/S0021-9258(19)44215-4","volume":"248","author":"Korn E. D.","year":"1973","journal-title":"J. Biol. 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E.","year":"2002"},{"key":"e_1_2_6_87_2","unstructured":"For selected reviews concerning silyloxy furan3\u2009asee:"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462338"},{"key":"e_1_2_6_88_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462338"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1217350"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100304n"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101269"},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1290981"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1289635"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900166"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob05822c"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200810"},{"key":"e_1_2_6_97_2","unstructured":"\u00a0"},{"key":"e_1_2_6_98_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460953"},{"key":"e_1_2_6_98_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460953"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200500497"},{"key":"e_1_2_6_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol060077d"},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol703065x"},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802359"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc00996b"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903077"},{"key":"e_1_2_6_105_2","unstructured":"For reviews on sulfoximine ligands in asymmetric metal catalysis see:"},{"key":"e_1_2_6_106_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2004.482"},{"key":"e_1_2_6_107_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527610648.ch2a"},{"key":"e_1_2_6_108_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.09.068"},{"key":"e_1_2_6_109_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527623235.ch6"},{"key":"e_1_2_6_110_2","unstructured":"Although the use of toluene and THF led to good stereoselectivities the total value of these syntheses suffered from rather moderate yields of the \u03b3\u2010(hydroxyalkyl)lactone1a(Table\u20051 entries\u20052 and 3). Therefore we also investigated the impact of TFE in these solvents and found that it significantly increased the yields of1aup to 87\u2009%. Unfortunately the stereoselectivities were not improved (96\u2009% de\u2005and 88\u2009%eewith toluene 99\u2009% de\u2005and 93\u2009%eewith THF)."},{"key":"e_1_2_6_111_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules17089010"},{"key":"e_1_2_6_112_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460394"},{"key":"e_1_2_6_112_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460394"},{"key":"e_1_2_6_113_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204921"},{"key":"e_1_2_6_113_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204921"},{"key":"e_1_2_6_114_2","unstructured":"\u00a0"},{"key":"e_1_2_6_115_2","doi-asserted-by":"publisher","DOI":"10.1080\/10426500802583553"},{"key":"e_1_2_6_116_2","doi-asserted-by":"publisher","DOI":"10.1021\/jf305153h"},{"key":"e_1_2_6_117_2","unstructured":"\u00a0"},{"key":"e_1_2_6_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/jf104247w"},{"key":"e_1_2_6_119_2","unstructured":"AGROW2012 640 20."},{"key":"e_1_2_6_120_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc36656h"},{"key":"e_1_2_6_121_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo070638u"},{"key":"e_1_2_6_122_2","unstructured":"The major stereoisomer ofsyn\u20104ewas formed with a loweeof 23\u2009%. See the Supporting Information."},{"key":"e_1_2_6_123_2","unstructured":"CCDC\u2005950558 and CCDC 950559 contain the crystallographic data for (S R)\u20101aandrac anti\u20101o respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif. Regarding the publication of Miao and co\u2010workers in ref. 30 we must note that several discrepancies were found in the stereochemical representation of their crystal structure and the chemical drawings of their catalysis products."},{"key":"e_1_2_6_124_2","doi-asserted-by":"publisher","DOI":"10.1107\/S090744490804362X"},{"key":"e_1_2_6_125_2","unstructured":"For recent comments on upholding scientific standards see:"},{"key":"e_1_2_6_126_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204076"},{"key":"e_1_2_6_126_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204076"},{"key":"e_1_2_6_127_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201201128"},{"key":"e_1_2_6_128_2","unstructured":"\u00a0"},{"key":"e_1_2_6_129_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00162-6"},{"key":"e_1_2_6_130_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo972031r"},{"key":"e_1_2_6_131_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc02438d"},{"key":"e_1_2_6_132_2","unstructured":"Tests on biological activity are carried out currently."},{"key":"e_1_2_6_133_2","unstructured":"Compared to the reactions conditions of Miao and co\u2010workers in Ref.\u200530 the catalyst reported here gives higher yields is more stereoselective and shows better reactivity for aliphatic phosphonates. Additionally the reactions proceed at much milder temperature and less amount of the nucleophile is required."},{"key":"e_1_2_6_134_2","unstructured":"The (R)\u2010 and (S)\u2010enantiomer of amino sulfoximineL1are commercially available hence allowing easy access to both product enantiomers."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201304331","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201304331","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:14:42Z","timestamp":1760264082000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201304331"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,1,8]]},"references-count":143,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2014,2,3]]}},"alternative-id":["10.1002\/chem.201304331"],"URL":"https:\/\/doi.org\/10.1002\/chem.201304331","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,1,8]]}}}