Stereoselective synthesis of C-glycosides from carboxylic acids: the tandem Tebbe–Claisen approach

Abstract

A variety of β- or α-C-glycosides may be readily accessed in an entirely stereoselective fashion from esters derived from the reaction of carboxylic acids and 3-hydroxy glycals, by way of a tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. Though of wide scope, for example allowing the synthesis of 1–6 linked C-disaccharides, the methodology does not currently allow the synthesis of C-glycosyl α-amino acids.