Catalytic Glycosylation with Rhodium(III)-Triphos Catalysts

Abstract

The formation of glycosides in high yield from 1-hydroxy sugars using catalytic amounts (0.5mol%) of Rh(III)Cl3(triphos) (1a) or [Rh(III)(MeCN)3(triphos)](TfO)3 (1b) is described. High stereocontrol at the anomeric center is achieved by neighboring group participation. In addition, an application of this new glycosylation procedure for the synthesis of a derivative of the oviposition-deterring pheromone of the cherry fruit fly Rhagoletis cerasi is presented.