A two-step, one-pot Baeyer-Villiger oxidation of biomass-derived levoglucosenone derivatives to chiral, C4-sustituted 5-hydroxymethyl butyrolactones

Andrew Cummings; Clare Rice; Gary N. Sheldrake; Christopher W. J. Murnaghan

doi:10.1002/ejoc.202401320

A two-step, one-pot Baeyer-Villiger oxidation of biomass-derived levoglucosenone derivatives to chiral, C4-sustituted 5-hydroxymethyl butyrolactones

Andrew Cummings, Clare Rice, Gary N. Sheldrake, Christopher W. J. Murnaghan^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

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Abstract

A two-step one-pot rapid microwave assisted method has been developed for the Baeyer-Villiger oxidation of biomass derived levoglucosenone (LGO) analogues. This method uses the acidic resin Amberlyst 15 as the catalyst and hydrogen peroxide as the oxidant in ethanol solution. A small library of C4-substituted LGO analogues have been synthesised and oxidised using this method giving high yields in short times in each case. The purity of the recovered products was very high removing the need for chromatographic separation.

Original language	English
Article number	e202401320
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	28
Issue number	10
Early online date	14 Feb 2025
DOIs	https://doi.org/10.1002/ejoc.202401320
Publication status	Published - 10 Mar 2025

Keywords

Baeyer-Villiger
oxidation of biomass-derived levoglucosenone derivatives
chiral
C4-sustituted 5-hydroxymethyl butyrolactones

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10.1002/ejoc.202401320Licence: CC BY

A two-step, one-pot Baeyer-Villiger oxidation of biomass-derived levoglucosenone derivatives to chiral, C4-sustituted 5-hydroxymethyl butyrolactones
Copyright 2025 The Authors. This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 1.17 MBLicence: CC BY

Cite this

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title = "A two-step, one-pot Baeyer-Villiger oxidation of biomass-derived levoglucosenone derivatives to chiral, C4-sustituted 5-hydroxymethyl butyrolactones",

abstract = "A two-step one-pot rapid microwave assisted method has been developed for the Baeyer-Villiger oxidation of biomass derived levoglucosenone (LGO) analogues. This method uses the acidic resin Amberlyst 15 as the catalyst and hydrogen peroxide as the oxidant in ethanol solution. A small library of C4-substituted LGO analogues have been synthesised and oxidised using this method giving high yields in short times in each case. The purity of the recovered products was very high removing the need for chromatographic separation.",

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AU - Cummings, Andrew

AU - Rice, Clare

AU - Sheldrake, Gary N.

AU - Murnaghan, Christopher W. J.

PY - 2025/3/10

Y1 - 2025/3/10

N2 - A two-step one-pot rapid microwave assisted method has been developed for the Baeyer-Villiger oxidation of biomass derived levoglucosenone (LGO) analogues. This method uses the acidic resin Amberlyst 15 as the catalyst and hydrogen peroxide as the oxidant in ethanol solution. A small library of C4-substituted LGO analogues have been synthesised and oxidised using this method giving high yields in short times in each case. The purity of the recovered products was very high removing the need for chromatographic separation.

AB - A two-step one-pot rapid microwave assisted method has been developed for the Baeyer-Villiger oxidation of biomass derived levoglucosenone (LGO) analogues. This method uses the acidic resin Amberlyst 15 as the catalyst and hydrogen peroxide as the oxidant in ethanol solution. A small library of C4-substituted LGO analogues have been synthesised and oxidised using this method giving high yields in short times in each case. The purity of the recovered products was very high removing the need for chromatographic separation.

KW - Baeyer-Villiger

KW - oxidation of biomass-derived levoglucosenone derivatives

KW - chiral

KW - C4-sustituted 5-hydroxymethyl butyrolactones

U2 - 10.1002/ejoc.202401320

DO - 10.1002/ejoc.202401320

M3 - Article

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VL - 28

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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M1 - e202401320

ER -

A two-step, one-pot Baeyer-Villiger oxidation of biomass-derived levoglucosenone derivatives to chiral, C4-sustituted 5-hydroxymethyl butyrolactones

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Keywords

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