{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T00:36:25Z","timestamp":1760574985062,"version":"build-2065373602"},"reference-count":49,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2011,9,19]],"date-time":"2011-09-19T00:00:00Z","timestamp":1316390400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2011,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Recently, we reported the use of a sequence of alkylation and dehydration methodologies to obtain new non\u2010proteinogenic amino acids (<jats:italic>N<\/jats:italic>\u2010ethyl \u03b1,\u03b2\u2010dehydroamino acids) from the methyl esters of <jats:italic>N<\/jats:italic>\u2010(4\u2010nitrophenylsulfonyl) \u03b2\u2010hydroxy amino acids. Thus, it was possible to obtain for the first time, non\u2010natural amino acids that incorporate both <jats:italic>N<\/jats:italic>\u2010ethyl and \u03b1,\u03b2\u2010dehydro moieties. Herein, we report the application of this <jats:italic>N<\/jats:italic>\u2010alkylation procedure to several methyl esters of \u03b2,\u03b2\u2010dibromo and \u03b2\u2010bromo \u03b2\u2010substituted dehydroamino acids protected with standard amine protecting groups such as <jats:italic>tert<\/jats:italic>\u2010butyloxycarbonyl, benzyloxycarbonyl, and (4\u2010nitrobenzyl)oxycarbonyl, as well as acyl and sulfonyl groups. The procedure allows the synthesis of the methyl esters of <jats:italic>N<\/jats:italic>\u2010protected <jats:italic>N<\/jats:italic>\u2010ethyl \u03b2,\u03b2\u2010dibromo and <jats:italic>N<\/jats:italic>\u2010ethyl \u03b2\u2010bromo \u03b2\u2010substituted dehydroamino acids in fair to high yields. Some of these <jats:italic>N<\/jats:italic>\u2010ethylated dehydroamino acid derivatives were used as substrates in cross\u2010coupling reactions to give \u03b2,\u03b2\u2010disubstituted <jats:italic>N<\/jats:italic>\u2010ethyldehydroalanine derivatives.<\/jats:p>","DOI":"10.1002\/ejoc.201100907","type":"journal-article","created":{"date-parts":[[2011,9,19]],"date-time":"2011-09-19T06:34:51Z","timestamp":1316414091000},"page":"6764-6772","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis of New <i>N<\/i>\u2010Ethyl Dehydroamino Acid Derivatives: <i>N<\/i>\u2010Ethyl \u03b2,\u03b2\u2010Dibromo, <i>N<\/i>\u2010Ethyl \u03b2\u2010Bromo \u03b2\u2010Substituted, and <i>N<\/i>\u2010Ethyl \u03b2,\u03b2\u2010Disubstituted <i>N<\/i>\u2010Protected Dehydroamino Acid Methyl Esters"],"prefix":"10.1002","volume":"2011","author":[{"given":"Lu\u00eds S.","family":"Monteiro","sequence":"first","affiliation":[]},{"given":"Juliana J.","family":"Andrade","sequence":"additional","affiliation":[]},{"given":"Ana C.","family":"Su\u00e1rez","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2011,9,19]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/b-003-111718"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020147q"},{"key":"e_1_2_6_4_2","first-page":"2701","author":"Rilatt I.","year":"2005","journal-title":"Synlett"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030024z"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19850970205"},{"key":"e_1_2_6_7_2","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00017a037"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(97)00107-7"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00238a005"},{"key":"e_1_2_6_11_2","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1007\/s007060070057"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1387(199901)5:1<56::AID-PSC186>3.0.CO;2-J"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1139\/v77-198"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1139\/v73-286"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2008.03.025"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.48-0324"},{"key":"e_1_2_6_18_2","unstructured":"C. Athanassopoulos H. L. S. Maia L. S. Monteiro D. Papaioannou Peptides1996: Proceedings of the 24th European Peptide Symposium(Eds.: R. Ramage R. Epton) Mayflower Scientific Ltd. Kingswinford U. K. 1998 pp. 219\u2013220."},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b705034h"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000256"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.198519851117"},{"key":"e_1_2_6_22_2","unstructured":"\u00a0"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00066a061"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/np970045m"},{"key":"e_1_2_6_25_2","unstructured":"\u00a0"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00040a024"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19911030904"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030105v"},{"key":"e_1_2_6_29_2","unstructured":"\u00a0"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-7091-8545-2_3"},{"volume-title":"The Peptides, Analysis","year":"1983","author":"Noda K.","key":"e_1_2_6_31_2"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1988-27503"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)85989-X"},{"volume-title":"Peptides","year":"1983","author":"Mazur R. H.","key":"e_1_2_6_34_2"},{"key":"e_1_2_6_35_2","first-page":"1","author":"Bonauer C.","year":"2006","journal-title":"Synthesis"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/a904730a"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700669"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201001302"},{"key":"e_1_2_6_39_2","unstructured":"\u00a0"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500368"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600519"},{"key":"e_1_2_6_42_2","doi-asserted-by":"crossref","first-page":"3377","DOI":"10.1016\/S0040-4039(03)00709-3","volume":"44","author":"Silva N. O.","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.09.107"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.12.084"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.03.057"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800602"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106487h"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-009-0466-x"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200208)2002:15<2524::AID-EJOC2524>3.0.CO;2-W"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201100907","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201100907","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T10:35:17Z","timestamp":1760524517000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201100907"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,9,19]]},"references-count":49,"journal-issue":{"issue":"33","published-print":{"date-parts":[[2011,11]]}},"alternative-id":["10.1002\/ejoc.201100907"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201100907","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"type":"print","value":"1434-193X"},{"type":"electronic","value":"1099-0690"}],"subject":[],"published":{"date-parts":[[2011,9,19]]},"assertion":[{"value":"2011-06-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2011-09-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}