Abstract
The carbon-Ferrier rearrangement is the reaction of appropriately functionalised glycals, with a variety of carbon nucleophiles such as allyltrimethylsilanes, alkynyltrimethylsilanes, silyl cyanides etc. involving the corresponding nucleophilic addition at the anomeric carbon with concomitant loss of a substituent at C-3. This leads to double bond migration to give 2,3unsaturated sugars which act as useful chiral substrates for further manipulations in organic synthesis.
Highlights
IntroductionThe well-known Ferrier rearrangement[1] involves the reaction of a suitably protected 1,2-glycal with an alcohol under Lewis acid catalysis to form the corresponding 2,3-unsaturated 1-Oglycosides
The well-known Ferrier rearrangement[1] involves the reaction of a suitably protected 1,2-glycal with an alcohol under Lewis acid catalysis to form the corresponding 2,3-unsaturated 1-Oglycosides. Such 1-O-glycosides have been transformed into a variety of useful intermediates both in organic synthesis as well as in carbohydrate chemistry
Several catalysts and nucleophiles have been introduced in the literature addressing α/β-selectivity, mildness of the method, effect of solvent, effect of acid catalyst, and yields of the products
Summary
The well-known Ferrier rearrangement[1] involves the reaction of a suitably protected 1,2-glycal with an alcohol under Lewis acid catalysis to form the corresponding 2,3-unsaturated 1-Oglycosides. Such 1-O-glycosides have been transformed into a variety of useful intermediates both in organic synthesis as well as in carbohydrate chemistry. Several catalysts and nucleophiles have been introduced in the literature addressing α/β-selectivity, mildness of the method, effect of solvent, effect of acid (or Lewis acid) catalyst, and yields of the products. A brief account of several methods that have been reported in the literature since 1982 is presented
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