Rapid alcoholysis of cyclic esters using metal alkoxides: access to linear lactyllactate-grafted polyglycidol

Yimthachote, Supajittra; Phomphrai, Khamphee

doi:10.1039/d2nj05564c

New J. Chem.

2023

DOI: 10.1039/d2nj05564c

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Rapid alcoholysis of cyclic esters using metal alkoxides: access to linear lactyllactate-grafted polyglycidol

Supajittra Yimthachote

Khamphee Phomphrai

Abstract: A facile alcoholysis of L-lactide (LA) and lactones was developed using inexpensive and commercially available Al(OiPr)3 (1), Ti(OiPr)4 (2), and Zr(OiPr)4.iPrOH (3) yielding alkyl (S,S)-lactyllactates and hydroxy esters. Complex 1...

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2024

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Synthesis of ω‐Hydroxy Fatty Acid Alkyl Esters by Macrocyclic Lactones Alcoholysis Catalyzed by Homoleptic and Heteroleptic Zinc Aryloxides

Petrus,

Matuszak,

Kinzhybalo

2024

Chemistry An Asian Journal

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A series of zinc aryloxides, [Zn4(sal‐Me)8]‧2.5(C7H8) (1), [Zn4(sal‐Me)8]‧CH2Cl2 (2), [Zn4(μ3‐OR)2(sal‐R)6] (3) (for R = Me (0.51), Et (0.49)), [Zn4(μ3‐OMe)4(sal‐Me)4(HOMe)4] (4), [Zn(sal‐Me)2(py)2]∙THF (5), {[Zn(sal‐Me)2(tmbpy)]∙2(C6H5CH3)}n (6), [Zn2(sal‐Me)2(THF)2Cl2]∙0.5(C6H5CH3) (7), and [Zn4(μ3‐OMe)2(sal‐Me)4Cl2] (8) (Hsal‐Me = methyl salicylate, py = pyridine, tmbpy = 4,4ʹ‐trimethylenedipyridine) were obtained that have different nuclearities and central core topologies and contain ligands of different basicity and coordination abilities. Compounds 1–8 were synthesized in the reaction of Hsal‐Me with ZnEt2 in the presence or absence of additional MeOH or N‐donor ligands (py, tmbpy), as well as in the reaction of ZnCl2 and Hsal‐Me with different amounts of NaOMe in a mixture of THF/MeOH. The catalytic activity of 1–8 was tested in the syntheses of ω‐hydroxy fatty acid methyl esters by alcoholysis of pentadecanolide (PDL) and hexadecanolide (HDL). Compound 7 exhibited the highest catalytic activity in both reactions. Based on the crystal structure of 7, adding ZnCl2 to zinc aryloxides 1–6 and 8 was used as a novel approach to form enhanced‐activity molecular adducts for macrolactones alcoholysis.

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Synthesis of ω‐Hydroxy Fatty Acid Alkyl Esters by Macrocyclic Lactones Alcoholysis Catalyzed by Homoleptic and Heteroleptic Zinc Aryloxides

Petrus,

Matuszak,

Kinzhybalo

2024

Chemistry An Asian Journal

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Rapid alcoholysis of cyclic esters using metal alkoxides: access to linear lactyllactate-grafted polyglycidol

Abstract: A facile alcoholysis of L-lactide (LA) and lactones was developed using inexpensive and commercially available Al(OiPr)3 (1), Ti(OiPr)4 (2), and Zr(OiPr)4.iPrOH (3) yielding alkyl (S,S)-lactyllactates and hydroxy esters. Complex 1...

Cited by 1 publication

References 35 publications

Synthesis of ω‐Hydroxy Fatty Acid Alkyl Esters by Macrocyclic Lactones Alcoholysis Catalyzed by Homoleptic and Heteroleptic Zinc Aryloxides

Synthesis of ω‐Hydroxy Fatty Acid Alkyl Esters by Macrocyclic Lactones Alcoholysis Catalyzed by Homoleptic and Heteroleptic Zinc Aryloxides

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