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).

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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.

References

• Indium trichloride catalyzed Ferrier rearrangement – facile synthesis of 2,3-unsaturated glycosides Boga, S. B. and Balasubramanian K. K. Arkivoc (PN-1099A) pp 87-102 2004 [1] open access publication