Synthesis of new chiral monodentate phosphines and their use in asymmetric hydrogenation

Kathrin Junge, Günther Oehme, Axel Monsees, Thomas Riermeier, Uwe Dingerdissen, Matthias Beller

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96 Scopus citations

Abstract

A general synthesis of chiral 4,5-dihydro-3H-dinaphthophosphepines 1a-g is described. The resulting ligands represent a new class of monodentate chiral phosphines. First applications of 1a-g in the rhodium-catalyzed asymmetric hydrogenation of unsaturated carboxylic acid derivatives demonstrate the usefulness of our ligands. Enantioselectivities up to 95% ee for the hydrogenation of methyl α-acetamidocinnamate were obtained in the presence of 1d. This result represent the highest enantioselectivity reported for asymmetric hydrogenation in the presence of monodentate phosphines.

Original languageEnglish
Pages (from-to)4977-4980
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number28
DOIs
StatePublished - 8 Jul 2002
Externally publishedYes

Keywords

  • Asymmetric hydrogenation
  • Chiral P ligands
  • Rhodium

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