{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T21:44:23Z","timestamp":1790286263951,"version":"4.1.0"},"reference-count":70,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2014,6,24]],"date-time":"2014-06-24T00:00:00Z","timestamp":1403568000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2014,8,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>(Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine\u2010, uracil\u2010, and 5\u2010fluorouracil\u2010substituted diester donor\u2013acceptor cyclopropanes and their use in the indium\u2010 and tin\u2010catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products could be easily decarboxylated and reduced to the corresponding alcohols. The method gives access to a broad range of new (carbo)nucleoside analogues in only four or five steps and will be highly useful for the synthesis of libraries of bioactive compounds.<\/jats:p>","DOI":"10.1002\/anie.201404832","type":"journal-article","created":{"date-parts":[[2014,6,24]],"date-time":"2014-06-24T15:09:46Z","timestamp":1403622586000},"page":"8484-8487","source":"Crossref","is-referenced-by-count":114,"title":["Synthesis of (Carbo)nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes"],"prefix":"10.1002","volume":"53","author":[{"given":"Sophie","family":"Racine","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Florian","family":"de\u2005Nanteuil","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eloisa","family":"Serrano","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00e9r\u00f4me","family":"Waser","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,6,24]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","volume-title":"Modified Nucleosides in Biochemistry Biotechnology and Medicine","year":"2008"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2009.10.002"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2009.10.006"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2009.09.014"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijantimicag.2012.04.005"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd4010"},{"key":"e_1_2_2_8_2","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9580002294"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197004612"},{"key":"e_1_2_2_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19700821115"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00320-2"},{"key":"e_1_2_2_12_2","volume-title":"Handbook of Nucleoside Synthesis","author":"Vorbr\u00fcggen H.","year":"2001"},{"key":"e_1_2_2_13_2","volume-title":"Antiviral Nucleosides: Chiral Synthesis and Chemotherapy","year":"2003"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700946"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800464r"},{"key":"e_1_2_2_16_2","volume-title":"Chemical Synthesis of Nucleoside Analogues","year":"2013"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs00003f"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300202"},{"key":"e_1_2_2_19_2","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo015733w"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400079"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00210a064"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo990195x"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-967937"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(76)80055-X"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr2004822"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo972265a"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob06775g"},{"key":"e_1_2_2_29_2","unstructured":"[3+2] annulation with imido\u2010cyclopropanes:"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106255"},{"key":"e_1_2_2_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106255"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103971"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol203144v"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5024578"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401616a"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC45552A"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4020656"},{"key":"e_1_2_2_37_2","unstructured":"Reviews on donor\u2013acceptor cyclopropanes:"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010016n"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.10.077"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/b901245c"},{"key":"e_1_2_2_41_2","first-page":"3353","author":"De Simone F.","year":"2009","journal-title":"Synthesis"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1351\/PAC-CON-09-09-28"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mencom.2011.11.001"},{"key":"e_1_2_2_44_2","first-page":"2969","author":"Tang P.","year":"2012","journal-title":"Synthesis"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60238A"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309886"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309886"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200355f"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397919708007081"},{"key":"e_1_2_2_49_2","unstructured":"\u00a0"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197905331"},{"key":"e_1_2_2_50_3","first-page":"568","volume":"91","year":"1979","journal-title":"Angew. Chem."},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(200004)2000:8<1507::AID-EJOC1507>3.0.CO;2-K"},{"key":"e_1_2_2_52_2","unstructured":"\u00a0"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0446294"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800027"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1081\/SCC-100108223"},{"key":"e_1_2_2_56_2","unstructured":"\u00a0"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961779r"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00670-X"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mencom.2011.11.011"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.05.036"},{"key":"e_1_2_2_61_2","unstructured":"Cyclopropanation in absence of the Boc protecting group was not successful."},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2006.08.086"},{"key":"e_1_2_2_63_2","unstructured":"The stereochemistry of compounds8\u2009e 8\u2009i and9\u2009ahas been determined by X\u2010ray crystallography. CCDC\u2005995573 994735 and 994948 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. The stereochemistry of the other compounds has been assigned by analogy or NMR experiments. See Supporting Information for further details."},{"key":"e_1_2_2_64_2","unstructured":"The uracil\u2010 and 5\u2010fluorouracil\u2010substituted cyclopropanes were obtained using a similar synthetic sequence. In the case of the 5\u2010fluorouracil derivatives it was necessary to use a more stable benzoyl protecting group. See Supporting Information for further details."},{"key":"e_1_2_2_65_2","unstructured":"The diastereoselectivity in the decarboxylation step was usually high (>5:1 >20:1 for8\u2009c). The products are obtained under kinetic control but the rationalization of the high selectivity will require further investigations."},{"key":"e_1_2_2_66_2","unstructured":"Cyclopentylamine26was obtained in 94\u2009% yield from the [3+2] annulation of the corresponding dibenzylester\u2010substituted cyclopropane with enol ether17."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201404832","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201404832","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T15:44:06Z","timestamp":1697471046000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201404832"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,6,24]]},"references-count":70,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2014,8,4]]}},"alternative-id":["10.1002\/anie.201404832"],"URL":"https:\/\/doi.org\/10.1002\/anie.201404832","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,6,24]]}}}