Ferrier-II rearrangement

What is Ferrier-II rearrangement?

In 1979, Ferrier first reported a reaction that converts 5-enopyranosides into cyclohexanones using a mercury (II) salt, resulting in stereochemical control with predominantly trans relationships between substituents at 3 and 5 positions.

Ferrier-II rearrangement - general reaction scheme
ferrier-ii-rearrangement

R1, R2, R3, R= alkyl, benzyl, etc.

This reaction is known by various names such as Ferrier-II rearrangement, Ferrier-II carbocyclization, Ferrier carbocyclization, or Ferrier-II reaction to distinguish it from another reaction discovered by Ferrier, which is referred to as the Ferrier reaction.

The reaction is valuable for converting carbohydrates into carbosugars, myo-inositols, and other natural products.

References

Ferrier, R. J., “Unsaturated carbohydrates. Part 21. A carbocyclic ring closure of a hex-5-enopyranoside derivativeJ. Chem. Soc., Perkin Trans. 1, 1979, 1455-1458
DOI: 10.1039/P19790001455

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