Chiral fluorous phosphorus ligands based on the binaphthyl skeleton: synthesis and applications in asymmetric catalysis

Two enantiopure fluorous phosphines have been conveniently synthesized by combining palladium-catalyzed coupling reactions of easily available binaphthyl building-blocks with the introduction of fluorous ponytails onto aromatic compounds via ether bond formation. These new fluorous chiral phosphines have been tested as ligands in metal-catalyzed asymmetric transformations, the best results being obtained in the palladium-catalyzed asymmetric allylic substitution of 1,3-diphenyl-2-propenyl acetate affording the products of up to 87% e.e. (C) 2003 Elsevier Ltd. All rights reserved.