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Issue 9, 2018
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An inexpensive catalyst, Fe(acac)3, for regio/site-selective acylation of diols and carbohydrates containing a 1,2-cis-diol

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Abstract

This work describes the [Fe(acac)3] (acac = acetylacetonate)-catalyzed, regio/site-selective acylation of 1,2- and 1,3-diols and glycosides containing a cis-vicinal diol. The iron(III) catalysts initially formed cyclic dioxolane-type intermediates with substrates between the iron(III) species and vicinal diols, and the efficient and selective acylation of one hydroxyl group was subsequently achieved by adding acylation reagents in the presence of diisopropylethylamine (DIPEA) under mild conditions. This reaction generally produced high selectivities and highly isolated yields with the same protection pattern as that achieved with dibutyl tinoxide-mediated schemes.

Graphical abstract: An inexpensive catalyst, Fe(acac)3, for regio/site-selective acylation of diols and carbohydrates containing a 1,2-cis-diol

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Publication details

The article was received on 07 Feb 2018, accepted on 10 Apr 2018 and first published on 10 Apr 2018


Article type: Communication
DOI: 10.1039/C8GC00428E
Citation: Green Chem., 2018,20, 1987-1991
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    An inexpensive catalyst, Fe(acac)3, for regio/site-selective acylation of diols and carbohydrates containing a 1,2-cis-diol

    J. Lv, J. Ge, T. Luo and H. Dong, Green Chem., 2018, 20, 1987
    DOI: 10.1039/C8GC00428E

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