Efficient Production of Biomass‐Derived C4 Chiral Synthons in Aqueous Solution

• Published in: ChemCatChem 2017-11, Vol.9 (22), p.4179-4184
• Main Authors: Lin, Shaoying, Guo, Xiao, Qin, Kai, Feng, Lei, Zhang, Yahong, Tang, Yi
• Format: Article
• Language: English
• Subjects: Aldehydes; biomass; Carbohydrates; Catalysis; Chirality; Condensates; epimerization; Hexoses; Isomerization; retro-aldol reaction; synthons
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201700944

Carbohydrates are expected to replace petroleum and to become the base of industrial chemistry. Chirality is one particular area in which carbohydrates have a special potential advantage over petroleum resources. Herein, we report a catalytic approach for the direct production of d‐tetroses [i.e., d‐(−)‐erythrose and d‐(+)‐erythrulose] from d‐hexoses through a fast retro‐aldol process at 190 °C that achieves a yield of 46 % and completely retains the chiral centers in the final chiral synthon. The d‐tetrose products were further converted into their derivatives, thereby accomplishing transfer of chirality from natural chiral hexoses to high‐value‐added chiral chemicals. Our results also suggest that the product distribution for the conversion of d‐hexoses was determined by their isomerization and epimerization trends that competed with their corresponding retro‐aldol condensation processes. Transfer complete: A catalytic approach for the direct production of d‐tetroses in 46 % yield from d‐hexoses through a fast retro‐aldol process is developed; the chiral centers in the final chiral synthon are completely retained. The d‐tetrose products are further converted into their derivatives, thereby accomplishing transfer of chirality from natural chiral hexoses to high‐value‐added chiral chemicals.