Ferrier rearrangement

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.

References

* "Unsaturated Carbohydrates. Part21. A Carboxylic Ring Closure of a Hex-5-enopyranoside Derivative", Robert J. Ferrier, J. Chem. Soc., Perkin Trans. 1, 1979, 1455 [http://www.rsc.org/Publishing/Journals/P1/article.asp?doi=P19790001455]
*"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 [http://www.arkat-usa.org/ark/journal/2004/I08_Narasimhan/1099/1099.asp] open access publication


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