Ferrier rearrangement
From Wikipedia, the free encyclopedia
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.
[edit] 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
