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.

catalytic glycosylation - Rh(III)triphos catalysts - 1-hydroxy sugars - O-glycosides - oviposition-deterring pheromone

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