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Issue 3, 2020
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Use of lithium aryloxides as promoters for preparation of α-hydroxy acid esters

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Abstract

In this work, a hexanuclear lithium compound, [Li6(MesalO)6] (1), supported by a chelating ligand, namely methyl salicylato (MesalOH), was used as a precursor for preparation of the monomeric lithium aryloxides [Li(MesalO)(MesalOH)] (2) and [Li(MesalO)(MeOH)2] (3) via reactions with MesalOH or MeOH. These aryloxides were characterized by single-crystal X-ray diffraction, and spectroscopic and other analytical methods. The diffusion-ordered 1H NMR measurements revealed the retention of solid-state structures of 1 and 2 in THF-d8 solution. Experimental data obtained for 3 showed its decomposition into compound 1 and free MeOH. Compound 1 generated from 3 was also used as a catalyst for the alcoholysis of L-lactide (L-LA) and glycolide (GA) for the preparation of α-hydroxy acid esters. We established that during methanolysis in the presence of 1, L-LA was selectively transformed into methyl (S,S)-O-lactyllactate (MeL2), and GA was converted to methyl glycolate (MeG1) and oligoglycolate esters MeGn (n = 2, 3, and 4).

Graphical abstract: Use of lithium aryloxides as promoters for preparation of α-hydroxy acid esters

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Supplementary files

Article information


Submitted
10 Sep 2019
Accepted
13 Dec 2019
First published
14 Dec 2019

Dalton Trans., 2020,49, 866-876
Article type
Paper

Use of lithium aryloxides as promoters for preparation of α-hydroxy acid esters

R. Petrus, P. Fałat and P. Sobota, Dalton Trans., 2020, 49, 866
DOI: 10.1039/C9DT03631H

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