Catalytic glycosylation with rhodium(III)-triphos catalysts

The formation of glycosides in high yield from 1-hydroxy sugars using catalytic amounts (0.5mol%) of Rh(III)Cl 3 (triphos) (la) 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.