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Efficient Production of Biomass‐Derived C 4 Chiral Synthons in Aqueous Solution
Author(s) -
Lin Shaoying,
Guo Xiao,
Qin Kai,
Feng Lei,
Zhang Yahong,
Tang Yi
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700944
Subject(s) - synthon , chemistry , isomerization , chirality (physics) , aldol condensation , product distribution , aldol reaction , epimer , yield (engineering) , catalysis , organic chemistry , aqueous solution , green chemistry , reaction mechanism , physics , thermodynamics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
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.