600-17-9Relevant articles and documents
Rambaud
, p. 1348 ()
Influence of the Interaction between a Tin Catalyst and an Accelerator on the Formose-Inspired Synthesis of α-Hydroxy-γ-butyrolactone
Yamaguchi, Sho,Matsuo, Takeaki,Motokura, Ken,Miyaji, Akimitsu,Baba, Toshihide
, p. 1386 - 1391 (2016/04/20)
In this study, we focused on the tin-catalyzed transformation of formaldehyde into α-hydroxy-γ-butyrolactone (HBL) in the presence of an α-hydroxy carbonyl compound as the accelerator. The screening of various accelerators aided in clarifying the structural prerequisites of the accelerator for the formose-inspired synthesis of HBL. To investigate the influence of the interactions between the tin metal and the accelerator on the catalytic activity, we performed a deuterium-exchange experiment with α-hydroxyacetophenone followed by in situ 119Sn NMR spectroscopy and X-ray absorption fine structure measurements. On the basis of the experimental results, we proposed a reaction mechanism to obtain HBL.
Mechanistic Insight into a Sugar-Accelerated Tin-Catalyzed Cascade Synthesis of α-Hydroxy-γ-butyrolactone from Formaldehyde
Yamaguchi, Sho,Matsuo, Takeaki,Motokura, Ken,Sakamoto, Yasuharu,Miyaji, Akimitsu,Baba, Toshihide
, p. 3661 - 3667 (2015/11/17)
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.
