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revised on 05.05.2019 and posted on 06.05.2019by Meifeng Wang, Gan Zhu, Yiqun Li, Liuqun Gu
acids were widely used as efficient catalysts in direct amide formation and
other organic transformations. Surprisingly, reports on their use as catalysts
in carbohydrates synthesis are very rare even though boron acid-diol
complexation was extensively investigated in molecular recognition for
saccharides and so on. Here we developed an efficient arylboronic acids
catalyzed dimerization of glucosamines forming deoxyfructosazine which is
important compound in pharmaceutical and food industries, against a commonly
held belief that excess amount of phenyl boronic acid (or boric acid) is a must.
A catalytic mechanism was also proposed and arylboronic acids instead of their
boronates was identified as catalysts.