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

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 ce...

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2018-01, Vol.2 (11), p.2455-2458
Main Authors: Bonneau, Guillaume, Peru, Aurélien A. M, Flourat, Amandine L, Allais, Florent
Format: Article
Language:English
Subjects:
Butyrolactone
Catalysis
Cellulose
Chemical Sciences
Chemical synthesis
Distillation
Fine chemicals
Fragrances
Green chemistry
Hydrogen peroxide
Organic chemistry
Oxidation
Oxidizing agents
Pheromones
Solvents
Sustainability
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 H 2 O 2 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. Aqueous H 2 O 2 -mediated Baeyer-Villiger oxidation of levoglucosenone provides valuable chiral lactone HBO in one step without an organic solvent, catalyst nor acid.
ISSN:1463-9262
1463-9270
DOI:10.1039/c8gc00553b