{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T01:49:43Z","timestamp":1788400183967,"version":"build-2803163510"},"reference-count":40,"publisher":"Wiley","issue":"34","license":[{"start":{"date-parts":[[2020,5,26]],"date-time":"2020-05-26T00:00:00Z","timestamp":1590451200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100004330","name":"GlaxoSmithKline","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100004330","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/P510592\/1"],"award-info":[{"award-number":["EP\/P510592\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2020,6,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A late\u2010stage functionalization of the aromatic ring in amino acid derivatives is described. The key step is a copper\u2010catalysed diversification of a boronate ester by amination (Chan\u2013Lam reaction) that can be carried out on a complex \u03b2\u2010aryl\u2010\u03b2\u2010amino acid scaffold. This not only considerably extends the substrate scope of amination partners, but also delivers an array of potent and selective integrin inhibitors as potential treatment agents of idiopathic pulmonary fibrosis (IPF). This versatile chemical strategy, which is amenable to high\u2010throughput\u2010array protocols, allows the installation of pharmaceutically valuable heteroaromatic fragments at a late stage by direct coupling to NH heterocycles, leading to compounds with drug\u2010like attributes. It thus constitutes a useful addition to the medicinal chemist's repertoire.<\/jats:p>","DOI":"10.1002\/chem.202001059","type":"journal-article","created":{"date-parts":[[2020,3,4]],"date-time":"2020-03-04T10:17:06Z","timestamp":1583317026000},"page":"7678-7684","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Late\u2010Stage Functionalization by Chan\u2013Lam Amination: Rapid Access to Potent and Selective Integrin Inhibitors"],"prefix":"10.1002","volume":"26","author":[{"given":"Henry","family":"Robinson","sequence":"first","affiliation":[{"name":"School of Chemistry GSK Carbon Neutral Laboratories for Sustainable Chemistry University of Nottingham  Jubilee Campus, Triumph Road Nottingham NG7 2TU UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Steven A.","family":"Oatley","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"James E.","family":"Rowedder","sequence":"additional","affiliation":[{"name":"Medicinal Science &amp; Technology GlaxoSmithKline Medicines Research Centre  Gunnels Wood Road Stevenage SG1 2NY UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pawel","family":"Slade","sequence":"additional","affiliation":[{"name":"Medicinal Science &amp; Technology GlaxoSmithKline Medicines Research Centre  Gunnels Wood Road Stevenage SG1 2NY UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simon J. F.","family":"Macdonald","sequence":"additional","affiliation":[{"name":"Medicinal Science &amp; Technology GlaxoSmithKline Medicines Research Centre  Gunnels Wood Road Stevenage SG1 2NY UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen P.","family":"Argent","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan D.","family":"Hirst","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas","family":"McInally","sequence":"additional","affiliation":[{"name":"School of Chemistry GSK Carbon Neutral Laboratories for Sustainable Chemistry University of Nottingham  Jubilee Campus, Triumph Road Nottingham NG7 2TU UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0487-041X","authenticated-orcid":false,"given":"Christopher J.","family":"Moody","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Nottingham  University Park Nottingham NG7 2RD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,5,26]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01409"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00628G"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm400138z"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00503-6"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00502-4"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00504-8"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01735-3"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0346584"},{"key":"e_1_2_6_9_1","author":"Mennen S. M.","year":"2019","journal-title":"Org. Process Res. Dev."},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12800"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1136\/thx.2006.062836"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1164\/rccm.200602-163OC"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1136\/thx.2010.148031"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.2011.01247.x"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.3390\/jcm5090078"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.83.12.4167"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1177\/0192623311416259"},{"key":"e_1_2_6_18_1","volume-title":"Molecular Biology of the Cell","author":"Alberts B.","year":"2002"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1183\/09059180.00010909"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1183\/09031936.00210414"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1164\/rccm.200706-805OC"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707948"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201707948"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00228-018-2435-3"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml5002079"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b00959"},{"key":"e_1_2_6_26_1","unstructured":"N. A.Anderson B. J.Fallon J. M.Pritchard 2014 WO 2014\/154725 A1."},{"key":"e_1_2_6_27_1","unstructured":"N. A.Anderson I. B.Campbell M. H. J.Campbell-Crawford A. P.Hancock S.Lemma S. J. F.Macdonald 2014 WO2016\/046230 A1."},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900382t"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo400408t"},{"key":"e_1_2_6_30_1","unstructured":"In a parallel series of experiments by using ethyl bromoacetate in the Reformatsky reaction the ethyl ester analogue of amine9was Boc-protected and determined to have >97\u2009%eeby HPLC on a chiral stationary phase (Figure\u2005S2 Supporting Information)."},{"key":"e_1_2_6_31_1","unstructured":"L.Jiang D. J.Morgans G.Bergne C.Chen H.Li P.Andre R. L.Halcomb J.Cha T.Hom 2018 WO2018\/49068 A1."},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2008-1032184"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1042\/bj20020809"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2011.06.001"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm970530e"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1038\/nsmb.2905"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1069040"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci100031x"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci100436p"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.202001059","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202001059","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202001059","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202001059","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:54:37Z","timestamp":1760273677000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202001059"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,26]]},"references-count":40,"journal-issue":{"issue":"34","published-print":{"date-parts":[[2020,6,18]]}},"alternative-id":["10.1002\/chem.202001059"],"URL":"https:\/\/doi.org\/10.1002\/chem.202001059","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,5,26]]},"assertion":[{"value":"2020-02-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-05-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}