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

Biology

Queen's University Belfast

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

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
Pages (from-to)	1-9
Number of pages	9
Journal	European Journal of Organic Chemistry
Early online date	22 Jan 2025
DOIs	https://doi.org/10.1002/ejoc.202401320
Publication status	Published - 14 Feb 2025

Keywords

rapid microwave assisted method
Baeyer-Villiger oxidation
biomass derived levoglucosenone (LGO)
Amberlyst 15
purity
chromatographic separation

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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 ButyrolactonesFinal published version, 1.21 MBLicence: CC BY

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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.",

keywords = "rapid microwave assisted method, Baeyer-Villiger oxidation, biomass derived levoglucosenone (LGO), Amberlyst 15, purity, chromatographic separation",

author = "Andrew Cummings and Clare Rice and Sheldrake, {Gary N.} and Murnaghan, {Christopher W. J.}",

year = "2025",

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doi = "10.1002/ejoc.202401320",

language = "English",

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journal = "European Journal of Organic Chemistry",

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T1 - A Two‐Step, One‐Pot Baeyer‐Villiger Oxidation of Biomass‐Derived Levoglucosenone Derivatives to Chiral, C4‐Sustituted 5‐Hydroxymethyl Butyrolactones

AU - Cummings, Andrew

AU - Rice, Clare

AU - Sheldrake, Gary N.

AU - Murnaghan, Christopher W. J.

PY - 2025/2/14

Y1 - 2025/2/14

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 - rapid microwave assisted method

KW - Baeyer-Villiger oxidation

KW - biomass derived levoglucosenone (LGO)

KW - Amberlyst 15

KW - purity

KW - chromatographic separation

U2 - 10.1002/ejoc.202401320

DO - 10.1002/ejoc.202401320

M3 - Article (journal)

SN - 1099-0690

SP - 1

EP - 9

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

A Two‐Step, One‐Pot Baeyer‐Villiger Oxidation of Biomass‐Derived Levoglucosenone Derivatives to Chiral, C4‐Sustituted 5‐Hydroxymethyl Butyrolactones

Abstract

Keywords

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