An unexpected chelation-controlled Yb(OTf)(3)-catalyzed aminolysis and azidolysis of cyclitol epoxides.
A chelation-controlled aminolysis and azidolysis of cyclitol epoxides with Yb(OTf)(3) has been disclosed. The presence of a free OH group able to direct the coordination with the lanthanide seems essential for an efficient regiocontrol of the process.