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Issue 31, 2018
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Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

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Abstract

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.

Graphical abstract: Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

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Publication details

The article was received on 21 Jun 2018, accepted on 17 Jul 2018 and first published on 18 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01464G
Citation: Org. Biomol. Chem., 2018,16, 5591-5597
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    Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

    B. Ren, L. Gan, L. Zhang, N. Yan and H. Dong, Org. Biomol. Chem., 2018, 16, 5591
    DOI: 10.1039/C8OB01464G

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