{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,23]],"date-time":"2025-12-23T10:29:55Z","timestamp":1766485795071,"version":"build-2065373602"},"reference-count":20,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2006,5,18]],"date-time":"2006-05-18T00:00:00Z","timestamp":1147910400000},"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":[[2006,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The methyl ester of <jats:italic>N<\/jats:italic>\u2010<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl\u2010(<jats:italic>Z<\/jats:italic>)\u2010\u03b2\u2010bromo\u2010\u03b2\u2010(1,2,4\u2010triazol\u20101\u2010yl)dehydroalanine was prepared by treatment of the methyl ester of <jats:italic>N<\/jats:italic>\u2010<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl\u2010(<jats:italic>E<\/jats:italic>)\u2010\u03b2\u2010(1,2,4\u2010triazol\u20101\u2010yl)dehydroalanine with <jats:italic>N<\/jats:italic>\u2010bromosuccinimide (NBS), followed by Et<jats:sub>3<\/jats:sub>N. The reactivities of this compound and of our previously synthesized methyl ester of <jats:italic>N<\/jats:italic>\u2010<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl\u2010\u03b2,\u03b2\u2010dibromodehydroalanine towards several nucleophiles were studied, and it was found that these compounds react with oxygen nucleophiles to give the corresponding \u03b1\u2010alkoxy\u2010\u03b2,\u03b2\u2010disubstituted alanines. Addition to the \u03b1\u2010carbon atom also occurred when the \u03b2,\u03b2\u2010dibromodehydroalanine derivative was treated with primary amines, giving \u03b1\u2010amino\u2010\u03b2,\u03b2\u2010dibromoalanines. Treatment of the \u03b2\u2010bromo\u2010\u03b2\u2010(1,2,4\u2010triazol\u20101\u2010yl)dehydroalanine derivative with amines gave \u03b1\u2010(alkylamino)\u2010\u03b2\u2010(alkylimino)alanines in high yields. These iminoalanines afforded \u03b1\u2010aminoglycines when treated with silica in dichloromethane. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)<\/jats:p>","DOI":"10.1002\/ejoc.200600094","type":"journal-article","created":{"date-parts":[[2006,5,18]],"date-time":"2006-05-18T14:56:16Z","timestamp":1147964176000},"page":"3226-3234","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Synthesis and Reactivity of \u03b2\u2010Bromo\u2010\u03b2\u2010Substituted Dehydroalanines"],"prefix":"10.1002","volume":"2006","author":[{"given":"Paula M. T.","family":"Ferreira","sequence":"first","affiliation":[]},{"given":"Lu\u00eds S.","family":"Monteiro","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2006,6,26]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19931050905"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)00811-0"},{"key":"e_1_2_6_2_3","first-page":"2635","author":"Monteiro L. 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