초록
<P>Levoglucosenone (<B>LGO</B>), a valuable chiral platform chemical that can be efficiently produced from catalytic fast pyrolysis of cellulose, has been efficiently converted into optically pure (<I>S</I>)-γ-hydroxymethyl-α,β-butenolide (<B>HBO</B>) using a two-step sequence involving a lipase-mediated Baeyer–Villiger oxidation and an acid hydrolysis. In the same fashion, (<I>S</I>)-γ-hydroxymethyl-γ-butyrolactone (<B>2H-HBO</B>) was successfully obtained through a three-step sequence (Baeyer–Villiger, palladium-catalysed hydrogenation and acid hydrolysis). The use of solid buffers in the lipase-mediated Baeyer–Villiger oxidation has proved beneficial in two ways: not only the reaction time and the enzymatic load were both reduced four-fold (from 8 to 2 hours and 464 to 113 U mmol<SUP>−1</SUP>) to reach conversions ≥83%, but solid buffers also prevented lipase from denaturation, thus preserving its enzymatic activity and allowing its use for further oxidation cycles.</P><BR><BR><P>Graphic Abstract</P><P>Baeyer–Villiger oxidation of levoglucosenone with CAL-B and solid buffers provided valuable lactones in high yields in only 2 hours while allowing enzyme recyclability.<BR><IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c4gc01231c'><BR></P>