γ-aminoadamantanecarboxylic acids through direct C-H bond amidations
γ-aminoadamantanecarboxylic acids through direct C-H bond amidations
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DOI：
10.1002/ejoc.200600975
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发表时间：
2007-03-01
影响因子：
2.8
通讯作者：
Schreiner, Peter R.
中科院分区：
文献类型：
--
作者：
Wanka, Lukas;Cabrele, Chiara;Schreiner, Peter R.
利用无溴，直接C-H键酰胺化，我们已经合成了大量的各种金刚烷酰胺。取决于所用的前体，这些酰胺在水解裂解后直接产生药学活性的氨基金刚烷或γ-氨基金刚烷羧酸。这些严格的类似物的γ-氨基丁酸（GABA）的保护在C-和N-末端，我们合成了一些肽纳入γ-氨基金刚烷羧酸在溶液中，以及通过固相肽合成。这些肽在药物化学和有机催化中具有广阔的应用前景。((c)Wiley-VCH Verlag GmbH & Co.
Utilizing bromine-free, direct C-H bond amidations we have synthesized a large variety of adamantane amides. Depending on the precursors used these amides directly yield pharmaceutically active aminoadamantanes or gamma-aminoadamantanecarboxylic acids after hydrolytic cleavage. These rigid analogues of gamma-aminobutyric acid (GABA) were protected at the C- and N-termini and we synthesized a number of peptides incorporating gamma-aminoadamantanecarboxylic acids in solution as well as via solid phase peptide synthesis. These peptides are promising scaffolds for applications in medicinal chemistry as well as in organocatalysis. ((c) Wiley-VCH Verlag GmbH & Co.