Efficient Preparation of Apically Substituted Diamondoid Derivatives
Efficient Preparation of Apically Substituted Diamondoid Derivatives
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DOI：
10.1002/chin.201430060
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发表时间：
2014-01
期刊：
影响因子：
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通讯作者：
Paul Kahl;B. Tkachenko;Anatoliy A. Novikovsky;Jonathan Becker;J. Dahl;R. Carlson;A. Fokin;P. Schreiner
中科院分区：
文献类型：
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作者：
Paul Kahl;B. Tkachenko;Anatoliy A. Novikovsky;Jonathan Becker;J. Dahl;R. Carlson;A. Fokin;P. Schreiner
摘要 我们提出了一种有效的三步免色谱序列，用于利用叔丁基二甲基氯硅烷作为单甲硅烷基化剂，从相应的双顶端二醇制备二金刚烷、三金刚烷和[121]四金刚烷的顶端单羟基衍生物。该程序已成功应用于其他几种脂肪族和芳香族二醇的单保护。此外，通过4,9-二羟基金刚烷在三氟乙酸中的Ritter反应制备了在医药和材料科学方面具有巨大潜力的9-氨基金刚烷-4-羧酸。
Abstract We present an effective three-step chromatography-free sequence for the preparation of apical monohydroxy derivatives of diamantane, triamantane, and [121]tetramantane from the corresponding bis-apical diols utilizing tert-butyldimethylsilyl chloride as the monosilylating agent. The procedure was successfully applied to the monoprotection of several other aliphatic and aromatic diols. Additionally, 9-aminodiamantan-4-carboxylic acid, which has significant potential in medicinal and material sciences, was prepared through Ritter reaction of 4,9-dihydroxydiamantane in trifluoroacetic acid.