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

Guillaume Bonneau (1) , Aurélien A. M. Peru (1) , Amandine Flourat (1) , Florent Allais (1)

1 ABI - Agro-Biotechnologies Industrielles

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.

Domains: Organic chemistry; Catalysis

Guillaume Bonneau, Aurélien A. M. Peru, Amandine Flourat, Florent Allais. 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. Green Chemistry, 2018, 20 (11), pp.2455-2458. ⟨10.1039/c8gc00553b⟩. ⟨hal-03473084⟩