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American Chemical Society, Organometallics, 17(18), p. 3511-3518, 1999

DOI: 10.1021/om990302d

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

Journal article published in 1999 by Joan Albert, J. Magali Cadena, J. Magali Cadena, Jaume Granell ORCID, Guillermo Muller, Juan I. Ordinas, David Panyella, Carmen Puerta, Carolina Sañudo, Pedro Valerga
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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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).