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Issue 11, 2018
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Organic solvent- and catalyst-free Baeyer–Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene®): a sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone

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Abstract

A straightforward and sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide (HBO) and (S)-γ-hydroxymethyl-α,β-butyrolactone (2H-HBO), two valuable chemical platforms for the synthesis of fine chemicals such as drugs, pheromones, flavors and fragrances, has been optimized using renewable cellulose-based levoglucosenone (LGO) and Cyrene® as starting materials and aqueous H2O2 as both a solvent and an oxidizing agent. Combined with short-path distillation, this procedure provides enantiopure HBO and 2H-HBO in yield as high as 72% at the kilo scale.

Graphical abstract: Organic solvent- and catalyst-free Baeyer–Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene®): a sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone

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Article information


Submitted
17 Feb 2018
Accepted
19 Mar 2018
First published
19 Mar 2018

Green Chem., 2018,20, 2455-2458
Article type
Communication

Organic solvent- and catalyst-free Baeyer–Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene®): a sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone

G. Bonneau, A. A. M. Peru, A. L. Flourat and F. Allais, Green Chem., 2018, 20, 2455
DOI: 10.1039/C8GC00553B

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