College of Chemistry & Chemical Engineering, Xinyang Normal University, Nanhu Road 237, Xinyang, Henan 464000, P. R. China.
Org Biomol Chem. 2018 Aug 8;16(31):5591-5597. doi: 10.1039/c8ob01464g.
A diisopropylethylamine (DIPEA)-triggered, self-catalyzed, regioselective acylation of carbohydrates and diols is presented. The hydroxyl groups can be acylated by the corresponding anhydride in MeCN in the presence of a catalytic amount of DIPEA. This method is comparatively green and mild as it uses less organic base compared with other selective acylation methods. Mechanistic studies indicate that DIPEA reacts with the anhydride to form a carboxylate ion, and then the carboxylate ion could catalyze the selective acylation through a dual H-bonding interaction.
本文报道了一种二异丙基乙胺（DIPEA）触发的、自催化的、区域选择性的碳水化合物和二醇酰化反应。在催化量的 DIPEA 存在下，相应的酸酐可以在 MeCN 中酰化羟基。与其他选择性酰化方法相比，该方法使用的有机碱较少，因此相对环保且温和。机理研究表明，DIPEA 与酸酐反应生成羧酸根离子，然后羧酸根离子通过双重氢键相互作用可以催化选择性酰化反应。
