{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T13:51:05Z","timestamp":1790257865670,"version":"4.1.0"},"reference-count":86,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2018,11,2]],"date-time":"2018-11-02T00:00:00Z","timestamp":1541116800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003329","name":"Ministerio de Econom\u00eda y Competitividad","doi-asserted-by":"publisher","award":["CTQ2016-78395-P"],"award-info":[{"award-number":["CTQ2016-78395-P"]}],"id":[{"id":"10.13039\/501100003329","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003329","name":"Ministerio de Econom\u00eda y Competitividad","doi-asserted-by":"publisher","award":["RYC-2012-09873"],"award-info":[{"award-number":["RYC-2012-09873"]}],"id":[{"id":"10.13039\/501100003329","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000921","name":"European Cooperation in Science and Technology","doi-asserted-by":"publisher","award":["CA15106"],"award-info":[{"award-number":["CA15106"]}],"id":[{"id":"10.13039\/501100000921","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2018,11,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The Cu<jats:sup>I<\/jats:sup>\u2010catalyzed selective \u03b1\u2010alkylation of \u03b1\u2010amino acid and peptide derivatives with 2\u2010alkyl\u20101,3\u2010dioxolanes is reported. This oxidative coupling is distinguished by its site\u2010specificity, high diastereoselectivity, and chirality preservation and exhibits absolute chemoselectivity for <jats:italic>N<\/jats:italic>\u2010aryl glycine motifs over other amino acid units. Collectively, the method allows for the assembly of challenging quaternary centers, as well as compounds derived from natural products of high structural complexity, which may provide ample opportunities for late\u2010stage functionalization of peptides.<\/jats:p>","DOI":"10.1002\/cssc.201802216","type":"journal-article","created":{"date-parts":[[2018,10,15]],"date-time":"2018-10-15T07:17:08Z","timestamp":1539587828000},"page":"3893-3898","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Site\u2010Selective Cu\u2010Catalyzed Alkylation of \u03b1\u2010Amino Acids and Peptides toward the Assembly of Quaternary Centers"],"prefix":"10.1002","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0149-5485","authenticated-orcid":false,"given":"Marcos","family":"San\u2005Segundo","sequence":"first","affiliation":[{"name":"University of the Basque Country (UPV\/EHU) Department of Organic Chemistry I Joxe Mari Korta R&amp;D Center  Avda. Tolosa 72 20018 Donostia-San Sebasti\u00e1n Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9004-3842","authenticated-orcid":false,"given":"Arkaitz","family":"Correa","sequence":"additional","affiliation":[{"name":"University of the Basque Country (UPV\/EHU) Department of Organic Chemistry I Joxe Mari Korta R&amp;D Center  Avda. Tolosa 72 20018 Donostia-San Sebasti\u00e1n Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,11,2]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-61779-331-8"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527631841"},{"key":"e_1_2_2_4_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201806250"},{"key":"e_1_2_2_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201806250"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2018.05.011"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201800011"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2018.03.019"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.7b00536"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00022"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo502408z"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2014.10.003"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500200x"},{"key":"e_1_2_2_14_1","unstructured":"For selected recent examples see:"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804654"},{"key":"e_1_2_2_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201804654"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC04292B"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03973"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710136"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201710136"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801445"},{"key":"e_1_2_2_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201801445"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC00368H"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201706367"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201706367"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608648"},{"key":"e_1_2_2_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608648"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature18941"},{"key":"e_1_2_2_24_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00620"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1007\/s41061-016-0038-y"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304268"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304268"},{"key":"e_1_2_2_28_1","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610073"},{"key":"e_1_2_2_30_2","author":"Brandhofer T.","year":"2018","journal-title":"Eur. 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Likewise the use of 2-aryl-1 3-dioxolanes afforded complex mixtures of products. We hypothesized that the trapping of a strongly stabilized radical being both tertiary and benzylic radical might be slower than other side reactions such as homo-coupling or even water-assisted acetal-opening reactions:"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)01058-4"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr990101j"},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b03334"},{"key":"e_1_2_2_58_1","unstructured":"For CDCs between amides and cyclic ethers see:"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701508"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201400646"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol501485f"},{"key":"e_1_2_2_62_1","doi-asserted-by":"publisher","DOI":"10.1042\/bj3240001"},{"key":"e_1_2_2_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC03706A"},{"key":"e_1_2_2_64_1","unstructured":"This acetylated compound was unstable and rapidly decomposed. All attempts to perform the direct CDC of aldehydes and1\u2009afailed to provide the target acylation reaction which reinforced the notion that dioxolanes did not act as merely protecting groups in our process and not only tamed the reactivity toward the formation of the corresponding tertiary alkyl radical but also resulted in a more stable product."},{"key":"e_1_2_2_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b00715"},{"key":"e_1_2_2_66_1","unstructured":"\u00a0"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b06658"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00944"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3113559"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.201300117"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja211697s"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja201610c"},{"key":"e_1_2_2_73_1","unstructured":"CuI-catalyzed hydrogen abstraction reactions from the \u03b1-carbon ofN-aryl glycine derivatives are well established; see for example:"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201600539"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201109027"},{"key":"e_1_2_2_75_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201109027"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0809052106"},{"key":"e_1_2_2_77_1","unstructured":"At this stage the formation of speciesVIIby direct reaction of radical speciesIVwith in situ formedtBuOO radical species or Cu(OAc)(OOtBu) cannot be entirely ruled out (Scheme\u20053 route\u2005b)."}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcssc.201802216","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.201802216","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T15:39:09Z","timestamp":1760369949000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.201802216"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,2]]},"references-count":86,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2018,11,23]]}},"alternative-id":["10.1002\/cssc.201802216"],"URL":"https:\/\/doi.org\/10.1002\/cssc.201802216","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,11,2]]},"assertion":[{"value":"2018-09-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-11-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}