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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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Article information


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

Dalton Trans., 2020, Advance Article
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, Advance Article , DOI: 10.1039/C9DT03631H

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