Enzyme-like chemoselective acylation of alcohols in the presence of amines catalyzed by a tetranuclear zinc cluster
Enzyme-like chemoselective acylation of alcohols in the presence of amines catalyzed by a tetranuclear zinc cluster
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DOI：
10.1021/ja711349r
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发表时间：
2008-03-12
影响因子：
15
通讯作者：
Mashima, Kazushi
中科院分区：
文献类型：
--
作者：
Ohshima, Takashi;Iwasaki, Takanori;Mashima, Kazushi
醇和胺的酰化反应是最基本的反应之一。由于氨基比羟基具有更大的亲核性，因此会发生完全的n -酰化。只有酶促反应才能促进高选择性的o -酰化反应，目前还没有使用人工催化剂的例子。在这里，我们报道了四核锌簇Zn(4)(OCOCF(3))(6)O在伯烷基胺和仲烷基胺的存在下有效催化高度化学选择性的O-酰化。我们的研究结果表明，锌簇作为人工酶的核心结构具有很高的潜力，可以实现进一步的类酶化学选择反应。
Acylation of alcohols and amines is one of the most fundamental reactions. Due to the greater nucleophilicity of the amino group compared to the hydroxyl group, complete N-acylation occurs. Only an enzymatic reaction can promote a highly selective O-acylation reaction, and there are no examples using an artificial catalyst. Here we report that the tetranuclear zinc cluster Zn(4)(OCOCF(3))(6)O efficiently catalyzes highly chemoselective O-acylation in the presence of primary and secondary alkyl amines. Our results suggest the high potential of the zinc cluster as the core structure of an artificial enzyme to realize further enzyme-like chemoselective reactions.