Mechanistic Insight into a Sugar-Accelerated Tin-Catalyzed Cascade Synthesis of α-Hydroxy-γ-butyrolactone from Formaldehyde

Abstract

Applications of the formose reaction, which involves the formation of sugars from formaldehyde, have previously been confined to the selective synthesis of unprotected sugars. Herein, it is demonstrated that α-hydroxy-γ-butyrolactone (HBL), which is one of the most important intermediates in pharmaceutical syntheses, can be produced from paraformaldehyde. In the developed reaction system, homogeneous tin chloride exhibits high catalytic activity and the addition of mono- and disaccharides accelerates the formation of HBL. These observations suggest that the formose reaction may serve as a feasible pathway for the synthesis of important chemicals.

Keywords: carbohydrates; domino reactions; homogeneous catalysis; lactones; sustainable chemistry.