Arylboronic
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.
Design of C2-Symmetric Tetrahydropentalenes as New Chiral Diene Ligands for Highly Enantioselective Rh-Catalyzed Arylation of N-Tosylarylimines with Arylboronic Acids.