Organic solvent- and catalyst-free Baeyer-Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene (R)): a sustainable route to (S)-gamma-hydroxymethyl-alpha,beta-butenolide and (S)-gamma-hydroxymethyl-gamma-butyrolactone

摘要

A straightforward and sustainable route to (S)-gamma-hydroxymethyl-alpha,beta-butenolide (HBO) and (S)-gamma-hydroxymethyl-alpha,beta-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 levoglucose-none (LGO) and Cyrene (R) 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.