Ferrier rearrangement

The Ferrier rearrangement is an organic reaction that involves a nucleophilic substitution reaction combined with an allylic shift in a 2,3-Unsaturated glycoside (see glycals).



In this example of a Ferrier rearrangement tri-O-acetyl-D-glucal (OAc stands for acetate groups) reacts with methanol as the aglycon and Indium chloride as a Lewis acid in dichloromethane to a mixture 7:1 of the α (1) and β (2) anomer.

Further examples are shown below.