Resolution of Benzylcyclohexylphenylphosphine by Palladium(II)−Amine Metallacycles. A New Ligand for Asymmetric Hydrovinylation

Abstract

The synthesis of benzylcyclohexylphenylphosphine and its resolution by means of optically active palladium metallacycles are reported. The absolute configuration of (RC,SP)-[PdCl(C6H4CHMeNMe2)(PBzCyPh)] has been determined by single-crystal X-ray analyses. The allyl complex [Pd(η3-2-MeC3H4)(PBzCyPh)S]BF4, prepared in situ from [Pd(η3-2-MeC3H4)Cl(PBzCyPh)] and AgBF4 in CH2Cl2 solution, was used as a precatalyst for asymmetric hydrovinylation of styrene and 2-vinylnaphthalene. This system permits the synthesis of 3-phenyl-1-butene and 3-(2-naphthyl)-1-butene with good ee values working in very mild conditions of temperature (15 °C).