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

✍ Scribed by Jerôme Bayardon; Marco Cavazzini; David Maillard; Gianluca Pozzi; Silvio Quici; Denis Sinou

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
245 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

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.

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