{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,11]],"date-time":"2026-02-11T07:10:24Z","timestamp":1770793824326,"version":"3.50.0"},"reference-count":23,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2003,3,27]],"date-time":"2003-03-27T00:00:00Z","timestamp":1048723200000},"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":[[2003,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Several novel amino acids and dehydroamino acids containing the benzo[<jats:italic>b<\/jats:italic>]thiophene moiety were prepared by Michael addition or sequential Michael addition and palladium\u2010catalyzed C\u2212C or C\u2212N cross couplings. The substrates for Michael addition were the methyl esters of <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010bis(<jats:italic>tert<\/jats:italic>\u2010butyloxycarbonyl)dehydroalanine [Boc<jats:sub>2<\/jats:sub>\u2212\u0394Ala\u2212OMe] and <jats:italic>N<\/jats:italic>\u2010(4\u2010toluenesulfonyl)\u2010<jats:italic>N<\/jats:italic>\u2010(<jats:italic>tert<\/jats:italic>\u2010butyloxycarbonyl)dehydroalanine [Tos\u2212\u0394Ala(<jats:italic>N<\/jats:italic>\u2010Boc)\u2212OMe], and the nucleophiles were aromatic thiols and 3\u2010iodobenzylamine. The addition of mercaptobenzo[<jats:italic>b<\/jats:italic>]thiophenes directly to Tos\u2212\u0394Ala(<jats:italic>N<\/jats:italic>\u2010Boc)\u2212OMe gave stereoselectively, in good yields, the <jats:italic>E<\/jats:italic>\u2010isomer of the corresponding dehydrocysteine. When thiophenols and 3\u2010iodobenzylamine were used as nucleophiles the presence of an additional function (halogen or amine) allowed a subsequent palladium\u2010catalyzed cross\u2010coupling reaction with functionalized benzo[<jats:italic>b<\/jats:italic>]thiophenes (boronic acids, a halogen or an amine). Using this strategy, several racemic amino acid and dehydroamino acid derivatives, which are linked to the benzo[<jats:italic>b<\/jats:italic>]thiophene moiety by an aromatic spacer, were obtained in good yields. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2003)<\/jats:p>","DOI":"10.1002\/ejoc.200390212","type":"journal-article","created":{"date-parts":[[2003,3,28]],"date-time":"2003-03-28T08:59:48Z","timestamp":1048841988000},"page":"1537-1544","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Synthesis of Novel Amino Acids and Dehydroamino Acids Containing the Benzo[<i>b<\/i>]thiophene Moiety"],"prefix":"10.1002","volume":"2003","author":[{"given":"Ana\u00a0S.","family":"Abreu","sequence":"first","affiliation":[]},{"given":"Nat\u00e1lia\u00a0O.","family":"Silva","sequence":"additional","affiliation":[]},{"given":"Paula\u00a0M.\u00a0T.","family":"Ferreira","sequence":"additional","affiliation":[]},{"given":"Maria\u2010Jo\u00e3o\u00a0R.\u00a0P.","family":"Queiroz","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2003,3,27]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1988-27503"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199110513"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199312441"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(90)85176-G"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/a904730a"},{"key":"e_1_2_6_7_2","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/b003353g"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106487h"},{"key":"e_1_2_6_10_2","unstructured":"\u00a0"},{"key":"e_1_2_6_11_2","doi-asserted-by":"crossref","unstructured":"E. 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