Coordination Chemistry and Asymmetric Catalysis with a Chiral Diphosphonite

Jarl Ivar Vlugt, Jos Marie Johannes Paulusse, Eric J. Zijp, Jason A. Tijmensen, Allison M. Mills, Anthony L. Spek, Carmen Claver, Dieter Vogt

Research output: Contribution to journalArticleAcademic

22 Citations (Scopus)

Abstract

The improved synthesis of the chiral diphosphonite, XantBino (1), based on a xanthene backbone and bearing chiral binaphthyl groups on both P-atoms is described together with its PdII and RhI complexes. The 31P NMR spectra of both complexes point out that the two phosphorus atoms are chemically inequivalent. The complex cis-[PdCl2(1)] (2) is structurally characterized by NMR spectroscopy and X-ray crystallography. The molecular structure reveals an unusually small bite angle for this member of the xantphos family of only 100°. The rhodium-catalyzed asymmetric hydroformylation of styrene and vinyl acetate as well as the asymmetric hydrogenation of methyl (Z)-2-acetamidocinnamate, applying this chiral diphosphonite 1, are described. Low enantiomeric excesses are obtained in the asymmetric hydroformylation, while use of the catalyst precursor [Rh(cod)(1)]BF4 (3) results in a promising enantiomeric excess in the Rh-catalyzed asymmetric hydrogenation.
Original languageUndefined
Pages (from-to)4193-4201
JournalEuropean journal of inorganic chemistry
Volume2004
Issue number21
DOIs
Publication statusPublished - 2004

Keywords

  • IR-99616

Cite this

Vlugt, J. I., Paulusse, J. M. J., Zijp, E. J., Tijmensen, J. A., Mills, A. M., Spek, A. L., ... Vogt, D. (2004). Coordination Chemistry and Asymmetric Catalysis with a Chiral Diphosphonite. European journal of inorganic chemistry, 2004(21), 4193-4201. https://doi.org/10.1002/ejic.200400132