P-Stereogenic monophosphines with the 2-p-terphenylyl and 1-pyrenyl substituents. Application to Pd and Ru asymmetric catalysis

The synthesis of five optically pure P-stereogenic monophosphines of the type PPhArR, 1-pyrenyl is described

Pau Clavero; Arnald Grabulosa; Mercè Font-Bardia; Guillermo Muller

2014

Scholarcy highlights

  • The synthesis of five optically pure P-stereogenic monophosphines of the type PPhArR, 1-pyrenyl is described
  • Neutral palladium complexes appeared as mixtures of two diastereomers in solution according to NMR
  • The application of neutral Pd complexes to catalytic styrene hydrovinylation afforded moderate conversions, high chemoselectivities to 3-phenyl-1-butene and up to 43% ee with precursor 12a
  • Cationic Pd complexes were tested as catalytic precursors in allylic substitution of rac-3-acetoxy-1,3-diphenyl-1-propene, with the anion of dimethylmalonate and benzylamine as nucleophiles, obtaining full conversions and up to 80% ee in alkylation and 60% ee in amination with precursor 13a
  • Ruthenium complexes were used as catalytic precursors in transfer hydrogenation of acetophenone, with complete conversions after several hours but low enantioselectivities

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