Departamento de Química, Centro de Investigación en Síntesis Química, Universidad de La Rioja, 26006 Logroño, La Rioja, Spain.
CIC bioGUNE, Bizkaia Technology Park, Building 800, 48170 Derio, Spain.
J Org Chem. 2020 Mar 6;85(5):3134-3145. doi: 10.1021/acs.joc.9b03020. Epub 2020 Feb 19.
The highly diastereoselective 1,4-conjugate additions of several nitrogen nucleophiles to chiral bicyclic dehydroalanines have been assessed effectively at room temperature in good to excellent yields without needing any catalyst or additional base. This methodology is general, simple, oxygen and moisture tolerant, high-yielding, totally chemo- and stereoselective. This procedure offers an efficient and practical approach for the synthesis of -substituted α,β-diamino acids, such as 1-isohistidine, τ-histidinoalanine, β-benzylaminoalanine, β-(piperidin-1-yl)alanine, β-(azepan-1-yl)alanine, and fluorescent and ciprofloxacin-containing amino acid derivatives.
几种氮亲核试剂在室温下对手性双环脱氢丙氨酸的高非对映选择性 1,4-共轭加成已被有效评估，无需任何催化剂或额外碱，即可获得良好至优异的产率。该方法具有通用性、简单、耐氧耐湿、高产率、完全化学和立体选择性。该方法为合成 -取代的α,β-二氨基酸，如 1-组氨酸、τ-组氨酰丙氨酸、β-苄基氨基丙氨酸、β-(哌啶-1-基)丙氨酸、β-(氮杂环庚烷-1-基)丙氨酸以及荧光和含有环丙沙星的氨基酸衍生物提供了一种有效且实用的途径。
