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

Organic & Biomolecular Chemistry
Bo RenHai Dong

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.

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Citations

Oct 26, 2021·Chemistry : a European Journal·Stefanie Mayr, Hendrik Zipse

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Methods Mentioned

BETA
acylation
acetylation
NMR
column
column chromatography

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